PMC:7571312 / 71997-73221 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T556","span":{"begin":534,"end":535},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T557","span":{"begin":604,"end":607},"obj":"http://purl.obolibrary.org/obo/CLO_0001302"},{"id":"T558","span":{"begin":1017,"end":1019},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T559","span":{"begin":1055,"end":1060},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"(3S)-3-{[N-(1H-Benzimidazol-2-ylcarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (31)\nFollowing the procedure described for the preparation 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 but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and 1H-benzimidazole-2-carboxylic acid and making noncritical variations provided a crude yellow oil. This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 95 mg (72%) of the title compound as an off-white foam. 1H NMR (DMSO-d6) δ 13.32 (s, 1H), 8.89 (d, J = 8 Hz, 1H), 8.60 (d, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz, 1H), 7.59 (m, 5H), 7.29 (m, 2H), 5.20 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.56 (m, 2H), 3.12 (m, 2H), 2.30 (m, 1H), 2.01 (m, 2H), 1.83 (m, 1H), 1.65 (m, 4H), 0.92 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C29H31Cl2N5O6m/z 616.0 (M + H)+. Anal. calcd for C29H31Cl2N5O6: C, 56.50; H, 5.07; N, 11.36. Found: C, 57.28; H, 5.32; N, 11.35. HRMS (ESI+) calcd for C29H31Cl2N5O6+H1 616.1724, found 616.1729."}

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},{"id":"A32833","pred":"chebi_id","subj":"T73856","obj":"http://purl.obolibrary.org/obo/CHEBI_48502"},{"id":"A69335","pred":"chebi_id","subj":"T863","obj":"http://purl.obolibrary.org/obo/CHEBI_32630"},{"id":"A87092","pred":"chebi_id","subj":"T863","obj":"http://purl.obolibrary.org/obo/CHEBI_37904"},{"id":"A3183","pred":"chebi_id","subj":"T23817","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A89863","pred":"chebi_id","subj":"T56409","obj":"http://purl.obolibrary.org/obo/CHEBI_46629"},{"id":"A19345","pred":"chebi_id","subj":"T34890","obj":"http://purl.obolibrary.org/obo/CHEBI_41264"},{"id":"A45762","pred":"chebi_id","subj":"T868","obj":"http://purl.obolibrary.org/obo/CHEBI_48624"},{"id":"A55718","pred":"chebi_id","subj":"T54365","obj":"http://purl.obolibrary.org/obo/CHEBI_46117"},{"id":"A96823","pred":"chebi_id","subj":"T58462","obj":"http://purl.obolibrary.org/obo/CHEBI_41275"},{"id":"A81299","pred":"chebi_id","subj":"T80761","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A69110","pred":"chebi_id","subj":"T84904","obj":"http://purl.obolibrary.org/obo/CHEBI_36622"},{"id":"A41579","pred":"chebi_id","subj":"T45612","obj":"http://purl.obolibrary.org/obo/CHEBI_33575"},{"id":"A59290","pred":"chebi_id","subj":"T87122","obj":"http://purl.obolibrary.org/obo/CHEBI_37527"},{"id":"A27983","pred":"chebi_id","subj":"T875","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A45223","pred":"chebi_id","subj":"T89803","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A61289","pred":"chebi_id","subj":"T51988","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A19604","pred":"chebi_id","subj":"T54835","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A97242","pred":"chebi_id","subj":"T33731","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A25732","pred":"chebi_id","subj":"T92838","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A43058","pred":"chebi_id","subj":"T88564","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A77160","pred":"chebi_id","subj":"T60324","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A10525","pred":"chebi_id","subj":"T97684","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A11010","pred":"chebi_id","subj":"T80754","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A47276","pred":"chebi_id","subj":"T35133","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A6186","pred":"chebi_id","subj":"T60607","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A67880","pred":"chebi_id","subj":"T65260","obj":"http://purl.obolibrary.org/obo/CHEBI_73613"}],"text":"(3S)-3-{[N-(1H-Benzimidazol-2-ylcarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (31)\nFollowing the procedure described for the preparation 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 but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and 1H-benzimidazole-2-carboxylic acid and making noncritical variations provided a crude yellow oil. This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 95 mg (72%) of the title compound as an off-white foam. 1H NMR (DMSO-d6) δ 13.32 (s, 1H), 8.89 (d, J = 8 Hz, 1H), 8.60 (d, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz, 1H), 7.59 (m, 5H), 7.29 (m, 2H), 5.20 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.56 (m, 2H), 3.12 (m, 2H), 2.30 (m, 1H), 2.01 (m, 2H), 1.83 (m, 1H), 1.65 (m, 4H), 0.92 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C29H31Cl2N5O6m/z 616.0 (M + H)+. Anal. calcd for C29H31Cl2N5O6: C, 56.50; H, 5.07; N, 11.36. Found: C, 57.28; H, 5.32; N, 11.35. HRMS (ESI+) calcd for C29H31Cl2N5O6+H1 616.1724, found 616.1729."}

{"project":"LitCovid-sentences","denotations":[{"id":"T442","span":{"begin":0,"end":124},"obj":"Sentence"},{"id":"T443","span":{"begin":125,"end":553},"obj":"Sentence"},{"id":"T444","span":{"begin":554,"end":700},"obj":"Sentence"},{"id":"T445","span":{"begin":701,"end":1063},"obj":"Sentence"},{"id":"T446","span":{"begin":1064,"end":1123},"obj":"Sentence"},{"id":"T447","span":{"begin":1124,"end":1159},"obj":"Sentence"},{"id":"T448","span":{"begin":1160,"end":1224},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"(3S)-3-{[N-(1H-Benzimidazol-2-ylcarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (31)\nFollowing the procedure described for the preparation 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 but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and 1H-benzimidazole-2-carboxylic acid and making noncritical variations provided a crude yellow oil. This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 95 mg (72%) of the title compound as an off-white foam. 1H NMR (DMSO-d6) δ 13.32 (s, 1H), 8.89 (d, J = 8 Hz, 1H), 8.60 (d, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz, 1H), 7.59 (m, 5H), 7.29 (m, 2H), 5.20 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.56 (m, 2H), 3.12 (m, 2H), 2.30 (m, 1H), 2.01 (m, 2H), 1.83 (m, 1H), 1.65 (m, 4H), 0.92 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C29H31Cl2N5O6m/z 616.0 (M + H)+. Anal. calcd for C29H31Cl2N5O6: C, 56.50; H, 5.07; N, 11.36. Found: C, 57.28; H, 5.32; N, 11.35. HRMS (ESI+) calcd for C29H31Cl2N5O6+H1 616.1724, found 616.1729."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1563","span":{"begin":609,"end":617},"obj":"Chemical"},{"id":"1564","span":{"begin":618,"end":633},"obj":"Chemical"},{"id":"1565","span":{"begin":1080,"end":1093},"obj":"Chemical"},{"id":"1566","span":{"begin":1095,"end":1096},"obj":"Chemical"},{"id":"1567","span":{"begin":1114,"end":1115},"obj":"Chemical"},{"id":"1568","span":{"begin":1131,"end":1132},"obj":"Chemical"},{"id":"1569","span":{"begin":1150,"end":1151},"obj":"Chemical"},{"id":"1570","span":{"begin":1182,"end":1195},"obj":"Chemical"},{"id":"1571","span":{"begin":1160,"end":1164},"obj":"Disease"}],"attributes":[{"id":"A1563","pred":"tao:has_database_id","subj":"1563","obj":"MESH:D000432"},{"id":"A1564","pred":"tao:has_database_id","subj":"1564","obj":"MESH:D008752"},{"id":"A1566","pred":"tao:has_database_id","subj":"1566","obj":"MESH:D002244"},{"id":"A1567","pred":"tao:has_database_id","subj":"1567","obj":"MESH:D009584"},{"id":"A1568","pred":"tao:has_database_id","subj":"1568","obj":"MESH:D002244"},{"id":"A1569","pred":"tao:has_database_id","subj":"1569","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-(1H-Benzimidazol-2-ylcarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (31)\nFollowing the procedure described for the preparation 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 but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and 1H-benzimidazole-2-carboxylic acid and making noncritical variations provided a crude yellow oil. This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 95 mg (72%) of the title compound as an off-white foam. 1H NMR (DMSO-d6) δ 13.32 (s, 1H), 8.89 (d, J = 8 Hz, 1H), 8.60 (d, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz, 1H), 7.59 (m, 5H), 7.29 (m, 2H), 5.20 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.56 (m, 2H), 3.12 (m, 2H), 2.30 (m, 1H), 2.01 (m, 2H), 1.83 (m, 1H), 1.65 (m, 4H), 0.92 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C29H31Cl2N5O6m/z 616.0 (M + H)+. Anal. calcd for C29H31Cl2N5O6: C, 56.50; H, 5.07; N, 11.36. Found: C, 57.28; H, 5.32; N, 11.35. HRMS (ESI+) calcd for C29H31Cl2N5O6+H1 616.1724, found 616.1729."}