PMC:7571312 / 48510-50113 JSONTXT

{"project":"LitCovid-PD-FMA-UBERON","denotations":[{"id":"T93","span":{"begin":491,"end":494},"obj":"Body_part"}],"attributes":[{"id":"A93","pred":"fma_id","subj":"T93","obj":"http://purl.org/sig/ont/fma/fma20935"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)\nAn oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. Found: C, 59.41; H, 6.63; N, 10.68."}

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T459","span":{"begin":161,"end":162},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T460","span":{"begin":201,"end":203},"obj":"http://purl.obolibrary.org/obo/CLO_0050509"},{"id":"T461","span":{"begin":231,"end":232},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T462","span":{"begin":528,"end":529},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T463","span":{"begin":576,"end":577},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T464","span":{"begin":747,"end":754},"obj":"http://purl.obolibrary.org/obo/OBI_0100026"},{"id":"T465","span":{"begin":747,"end":754},"obj":"http://purl.obolibrary.org/obo/UBERON_0000468"},{"id":"T466","span":{"begin":942,"end":944},"obj":"http://purl.obolibrary.org/obo/CLO_0053799"},{"id":"T467","span":{"begin":972,"end":973},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T468","span":{"begin":1458,"end":1460},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T469","span":{"begin":1493,"end":1498},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)\nAn oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. Found: C, 59.41; H, 6.63; N, 10.68."}

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"id":"A94290","pred":"chebi_id","subj":"T74561","obj":"http://purl.obolibrary.org/obo/CHEBI_32772"},{"id":"A13025","pred":"chebi_id","subj":"T74561","obj":"http://purl.obolibrary.org/obo/CHEBI_44520"},{"id":"A86362","pred":"chebi_id","subj":"T65219","obj":"http://purl.obolibrary.org/obo/CHEBI_16881"},{"id":"A54064","pred":"chebi_id","subj":"T44034","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A64253","pred":"chebi_id","subj":"T41687","obj":"http://purl.obolibrary.org/obo/CHEBI_35581"},{"id":"A36418","pred":"chebi_id","subj":"T75707","obj":"http://purl.obolibrary.org/obo/CHEBI_23004"},{"id":"A11589","pred":"chebi_id","subj":"T75707","obj":"http://purl.obolibrary.org/obo/CHEBI_37622"},{"id":"A14503","pred":"chebi_id","subj":"T19","obj":"http://purl.obolibrary.org/obo/CHEBI_17741"},{"id":"A49000","pred":"chebi_id","subj":"T75923","obj":"http://purl.obolibrary.org/obo/CHEBI_17997"},{"id":"A91979","pred":"chebi_id","subj":"T30381","obj":"http://purl.obolibrary.org/obo/CHEBI_75958"},{"id":"A56970","pred":"chebi_id","subj":"T8447","obj":"http://purl.obolibrary.org/obo/CHEBI_53251"},{"id":"A35606","pred":"chebi_id","subj":"T16308","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A24867","pred":"chebi_id","subj":"T44169","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A61438","pred":"chebi_id","subj":"T72291","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A48113","pred":"chebi_id","subj":"T52737","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A37239","pred":"chebi_id","subj":"T27","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A56561","pred":"chebi_id","subj":"T47188","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A39450","pred":"chebi_id","subj":"T21947","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A42842","pred":"chebi_id","subj":"T62313","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A39661","pred":"chebi_id","subj":"T65167","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A27122","pred":"chebi_id","subj":"T7414","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A64179","pred":"chebi_id","subj":"T29594","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A20626","pred":"chebi_id","subj":"T13853","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A4732","pred":"chebi_id","subj":"T11215","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A93566","pred":"chebi_id","subj":"T84447","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A86407","pred":"chebi_id","subj":"T75855","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A96947","pred":"chebi_id","subj":"T35764","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A31755","pred":"chebi_id","subj":"T55887","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A55927","pred":"chebi_id","subj":"T7116","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A18905","pred":"chebi_id","subj":"T12321","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A38086","pred":"chebi_id","subj":"T67952","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A58210","pred":"chebi_id","subj":"T77336","obj":"http://purl.obolibrary.org/obo/CHEBI_73613"},{"id":"A49615","pred":"chebi_id","subj":"T73211","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)\nAn oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. Found: C, 59.41; H, 6.63; N, 10.68."}

{"project":"LitCovid-sentences","denotations":[{"id":"T320","span":{"begin":0,"end":116},"obj":"Sentence"},{"id":"T321","span":{"begin":117,"end":442},"obj":"Sentence"},{"id":"T322","span":{"begin":443,"end":616},"obj":"Sentence"},{"id":"T323","span":{"begin":617,"end":733},"obj":"Sentence"},{"id":"T324","span":{"begin":734,"end":839},"obj":"Sentence"},{"id":"T325","span":{"begin":840,"end":986},"obj":"Sentence"},{"id":"T326","span":{"begin":987,"end":1501},"obj":"Sentence"},{"id":"T327","span":{"begin":1502,"end":1567},"obj":"Sentence"},{"id":"T328","span":{"begin":1568,"end":1603},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)\nAn oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. Found: C, 59.41; H, 6.63; N, 10.68."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1142","span":{"begin":672,"end":677},"obj":"Chemical"},{"id":"1143","span":{"begin":706,"end":721},"obj":"Chemical"},{"id":"1144","span":{"begin":779,"end":784},"obj":"Chemical"},{"id":"1145","span":{"begin":798,"end":803},"obj":"Chemical"},{"id":"1146","span":{"begin":899,"end":907},"obj":"Chemical"},{"id":"1147","span":{"begin":908,"end":923},"obj":"Chemical"},{"id":"1148","span":{"begin":1518,"end":1528},"obj":"Chemical"},{"id":"1149","span":{"begin":1534,"end":1537},"obj":"Chemical"},{"id":"1150","span":{"begin":1539,"end":1540},"obj":"Chemical"},{"id":"1151","span":{"begin":1558,"end":1559},"obj":"Chemical"},{"id":"1152","span":{"begin":1575,"end":1576},"obj":"Chemical"},{"id":"1153","span":{"begin":1594,"end":1595},"obj":"Chemical"}],"attributes":[{"id":"A1142","pred":"tao:has_database_id","subj":"1142","obj":"MESH:D014867"},{"id":"A1143","pred":"tao:has_database_id","subj":"1143","obj":"MESH:D008752"},{"id":"A1144","pred":"tao:has_database_id","subj":"1144","obj":"MESH:D014867"},{"id":"A1145","pred":"tao:has_database_id","subj":"1145","obj":"MESH:C017082"},{"id":"A1146","pred":"tao:has_database_id","subj":"1146","obj":"MESH:D000432"},{"id":"A1147","pred":"tao:has_database_id","subj":"1147","obj":"MESH:D008752"},{"id":"A1150","pred":"tao:has_database_id","subj":"1150","obj":"MESH:D002244"},{"id":"A1151","pred":"tao:has_database_id","subj":"1151","obj":"MESH:D009584"},{"id":"A1152","pred":"tao:has_database_id","subj":"1152","obj":"MESH:D002244"},{"id":"A1153","pred":"tao:has_database_id","subj":"1153","obj":"MESH:D009584"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)\nAn oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. Found: C, 59.41; H, 6.63; N, 10.68."}