PMC:7571312 / 102809-103839 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T22","span":{"begin":371,"end":372},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T23","span":{"begin":522,"end":523},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T24","span":{"begin":983,"end":985},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T25","span":{"begin":1022,"end":1027},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"Following 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 N-(tert-butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide and making noncritical variations provided a crude green solid. This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 300 mg, 91%. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (d, J = 2.0 Hz, 1H), 8.68 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.37 (d, J = 7.1 Hz, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 7.07 (t, 1H), 6.97 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.68 (m, 1H), 4.38–4.49 (m, 3H), 3.88 (s, 3H), 2.97–3.17 (m, 4H), 2.20–2.32 (m, 1H), 2.02–2.14 (m, 1H), 1.93–2.02 (m, 1H), 1.52–1.69 (m, 2H); MS (APCI±) for C27H29N4O5Cl m/z 526.0 (M + H)−."}

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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 N-(tert-butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide and making noncritical variations provided a crude green solid. This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 300 mg, 91%. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (d, J = 2.0 Hz, 1H), 8.68 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.37 (d, J = 7.1 Hz, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 7.07 (t, 1H), 6.97 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.68 (m, 1H), 4.38–4.49 (m, 3H), 3.88 (s, 3H), 2.97–3.17 (m, 4H), 2.20–2.32 (m, 1H), 2.02–2.14 (m, 1H), 1.93–2.02 (m, 1H), 1.52–1.69 (m, 2H); MS (APCI±) for C27H29N4O5Cl m/z 526.0 (M + H)−."}

{"project":"LitCovid-sentences","denotations":[{"id":"T574","span":{"begin":0,"end":391},"obj":"Sentence"},{"id":"T575","span":{"begin":392,"end":549},"obj":"Sentence"},{"id":"T576","span":{"begin":550,"end":1030},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Following 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 N-(tert-butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide and making noncritical variations provided a crude green solid. This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 300 mg, 91%. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (d, J = 2.0 Hz, 1H), 8.68 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.37 (d, J = 7.1 Hz, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 7.07 (t, 1H), 6.97 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.68 (m, 1H), 4.38–4.49 (m, 3H), 3.88 (s, 3H), 2.97–3.17 (m, 4H), 2.20–2.32 (m, 1H), 2.02–2.14 (m, 1H), 1.93–2.02 (m, 1H), 1.52–1.69 (m, 2H); MS (APCI±) for C27H29N4O5Cl m/z 526.0 (M + H)−."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1896","span":{"begin":465,"end":473},"obj":"Chemical"},{"id":"1897","span":{"begin":474,"end":489},"obj":"Chemical"}],"attributes":[{"id":"A1896","pred":"tao:has_database_id","subj":"1896","obj":"MESH:D000432"},{"id":"A1897","pred":"tao:has_database_id","subj":"1897","obj":"MESH:D008752"}],"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":"Following 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 N-(tert-butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide and making noncritical variations provided a crude green solid. This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 300 mg, 91%. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (d, J = 2.0 Hz, 1H), 8.68 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.37 (d, J = 7.1 Hz, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 7.07 (t, 1H), 6.97 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.68 (m, 1H), 4.38–4.49 (m, 3H), 3.88 (s, 3H), 2.97–3.17 (m, 4H), 2.20–2.32 (m, 1H), 2.02–2.14 (m, 1H), 1.93–2.02 (m, 1H), 1.52–1.69 (m, 2H); MS (APCI±) for C27H29N4O5Cl m/z 526.0 (M + H)−."}