(7S)-4-chloro-9-(2,2-dimethylpropyl)-7-[2-oxo-2-[4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidin-1-yl]ethyl]-3,6,7,10-tetrahydropyrazolo[3,4-i][2]benzazepin-8-one → N-((R)-9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)-4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (7S)-4-chloro-9-(2,2-dimethylpropyl)-7-[2-oxo-2-[4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidin-1-yl]ethyl]-3,6,7,10-tetrahydropyrazolo[3,4-i][2]benzazepin-8-one | HCID 11979011 | — |
| Reactant | 3-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one | HCID 18321246 | — |
| Reactant | (S)-2-(9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid | HCID 59731963 | — |
| Product | N-((R)-9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)-4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxamide | HCID 11979017 | 33% |
Reaction Steps
(S)-2-(9-Benzyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid (80 mg, 0.24 mmol) and 3-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (75 mg, 0.33 mmol) were reacted in a manner analogous to the preparation of 4-Chloro-9-(2,2-dimethyl-propyl)-7-(S)-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one. Material was obtained as white solid in 33% yield. MS m/e (M+H)+=542.3. 1H NMR (500 MHz, DMSO-D6): δ=13.01 (s, 1H), 10.11 (s, 1H), 8.21 (s, 1H), 7.36 (d, J=7.93, 1H), 7.17 (m, 1H), 7.11 (m, 2H), 6.91 (m, 1H), 6.83 (d, J=7.63, 1H), 5.35 (d, J=17.09, 1H), 4.61 (d, J=17.40, 1H), 4.38 (m, 1H), 4.02 (m, 1H), 3.83 (s, 1H), 3.55 (t, J=12.36, 1H), 2.95 (m, 6H), 2.79 (m, 1H), 2.42 (m, 1H), 2.31 (m, 2H), 1.90 (m, 1H), 1.63 (m, 2H), 1.17 (m, 1H), 0.72 (d, J=9.77, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07384930B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-846e370d95c24d658b5377c2540c5867 |
| Source note | uspto-grants-2008_06 |