(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 → (7S)-9-Benzyl-7-(2-oxo-2-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperazin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one
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-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one | HCID 59731943 | — |
| 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 | (7S)-9-Benzyl-7-(2-oxo-2-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperazin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one | HCID 59731920 | 21% |
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-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one (75 mg, 0.32 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 21% yield. MS m/e (M+H)+=543.3. 1H NMR (500 MHz, DMSO-D6): δ=13.01(s, 1H), 10.13(s, 1H), 8.21(s, 1H), 7.36(d, J=8.54, 1H), 7.19(d, J=7.02, 1H), 7.11(m, 2H), 6.90(t, J=7.32, 1H), 6.82(d, J=7.93, 1H), 5.36(d, J=17.40, 1H), 4.61(d, J=17.09, 1H), 3.84(m, 1H), 3.57(d, J=13.12, 1H), 3.47(m, 2H), 3.38(m, 1H), 3.32(M, 1H), 3.09(m, 1H), 3.02(d, J=14.04, 1H), 2.985(m, 2H), 2.85(m, 1H), 2.75(m, 1H), 2.65(m, 3H), 2.50(m, 2H), 2.31(d, J=16.48, 1H), 0.71(s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07544680B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-d385aeec70174272a9f3896aa1b0a252 |
| Source note | uspto-grants-2009_06 |