PMC:7571312 / 105146-106424 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T30","span":{"begin":547,"end":548},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T31","span":{"begin":703,"end":704},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T32","span":{"begin":1066,"end":1068},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T33","span":{"begin":1103,"end":1108},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide\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 N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and indole-2-carboxylic acid and making no other critical variations provided a crude yellow foam. This material was purified by Biotage MPLC (40 M column, 2.5–3.5% methanol/chloroform) to afford 1.06 g (62%) of the title compound as a light yellow foam. 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.58 (d, J = 8 Hz, 1H), 8.50 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.62–4.50 (m, 3H), 4.45 (m, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.08 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H), 1.72–1.58 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H31ClN4O4m/z 475.1 (M + H)+; anal. calcd for C24H31ClN4O4·0.35 CHCl3: C, 56.59; H, 6.12; N, 10.84. Found: C, 56.38; H, 6.18; N, 10.75; HRMS (ESI+) calcd for C24H31ClN4O4 475.2107, found 475.2122."}

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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 N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and indole-2-carboxylic acid and making no other critical variations provided a crude yellow foam. This material was purified by Biotage MPLC (40 M column, 2.5–3.5% methanol/chloroform) to afford 1.06 g (62%) of the title compound as a light yellow foam. 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.58 (d, J = 8 Hz, 1H), 8.50 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.62–4.50 (m, 3H), 4.45 (m, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.08 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H), 1.72–1.58 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H31ClN4O4m/z 475.1 (M + H)+; anal. calcd for C24H31ClN4O4·0.35 CHCl3: C, 56.59; H, 6.12; N, 10.84. Found: C, 56.38; H, 6.18; N, 10.75; HRMS (ESI+) calcd for C24H31ClN4O4 475.2107, found 475.2122."}

{"project":"LitCovid-sentences","denotations":[{"id":"T582","span":{"begin":0,"end":135},"obj":"Sentence"},{"id":"T583","span":{"begin":136,"end":567},"obj":"Sentence"},{"id":"T584","span":{"begin":568,"end":723},"obj":"Sentence"},{"id":"T585","span":{"begin":724,"end":1181},"obj":"Sentence"},{"id":"T586","span":{"begin":1182,"end":1278},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide\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 N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and indole-2-carboxylic acid and making no other critical variations provided a crude yellow foam. This material was purified by Biotage MPLC (40 M column, 2.5–3.5% methanol/chloroform) to afford 1.06 g (62%) of the title compound as a light yellow foam. 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.58 (d, J = 8 Hz, 1H), 8.50 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.62–4.50 (m, 3H), 4.45 (m, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.08 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H), 1.72–1.58 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H31ClN4O4m/z 475.1 (M + H)+; anal. calcd for C24H31ClN4O4·0.35 CHCl3: C, 56.59; H, 6.12; N, 10.84. Found: C, 56.38; H, 6.18; N, 10.75; HRMS (ESI+) calcd for C24H31ClN4O4 475.2107, found 475.2122."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1924","span":{"begin":634,"end":642},"obj":"Chemical"},{"id":"1925","span":{"begin":643,"end":653},"obj":"Chemical"},{"id":"1926","span":{"begin":1128,"end":1140},"obj":"Chemical"},{"id":"1927","span":{"begin":1146,"end":1151},"obj":"Chemical"},{"id":"1928","span":{"begin":1153,"end":1154},"obj":"Chemical"},{"id":"1929","span":{"begin":1172,"end":1173},"obj":"Chemical"},{"id":"1930","span":{"begin":1189,"end":1190},"obj":"Chemical"},{"id":"1931","span":{"begin":1208,"end":1209},"obj":"Chemical"},{"id":"1932","span":{"begin":1240,"end":1252},"obj":"Chemical"},{"id":"1933","span":{"begin":1218,"end":1222},"obj":"Disease"}],"attributes":[{"id":"A1924","pred":"tao:has_database_id","subj":"1924","obj":"MESH:D000432"},{"id":"A1925","pred":"tao:has_database_id","subj":"1925","obj":"MESH:D002725"},{"id":"A1928","pred":"tao:has_database_id","subj":"1928","obj":"MESH:D002244"},{"id":"A1929","pred":"tao:has_database_id","subj":"1929","obj":"MESH:D009584"},{"id":"A1930","pred":"tao:has_database_id","subj":"1930","obj":"MESH:D002244"},{"id":"A1931","pred":"tao:has_database_id","subj":"1931","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":"N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide\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 N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and indole-2-carboxylic acid and making no other critical variations provided a crude yellow foam. This material was purified by Biotage MPLC (40 M column, 2.5–3.5% methanol/chloroform) to afford 1.06 g (62%) of the title compound as a light yellow foam. 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.58 (d, J = 8 Hz, 1H), 8.50 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.62–4.50 (m, 3H), 4.45 (m, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.08 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H), 1.72–1.58 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H31ClN4O4m/z 475.1 (M + H)+; anal. calcd for C24H31ClN4O4·0.35 CHCl3: C, 56.59; H, 6.12; N, 10.84. Found: C, 56.38; H, 6.18; N, 10.75; HRMS (ESI+) calcd for C24H31ClN4O4 475.2107, found 475.2122."}