HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate → {(S)-1-[1-(2-Cyano-phenyl)-1H-indazol-3-ylmethyl]-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate | HCID 22881971 | — |
| Reactant | 2-(3-Bromomethyl-indazol-1-yl)-benzonitrile | HCID 90037645 | — |
| Reactant | [(S)-1-(5-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester | HCID 90221057 | — |
| Product | {(S)-1-[1-(2-Cyano-phenyl)-1H-indazol-3-ylmethyl]-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-carbamic acid tert-butyl ester | HCID 90221209 | 72.9% |
Reaction Steps
In a similar manner to that described for the preparation of [(S)-1-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester (Intermediate 5), ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (Intermediate 2)(500 mg, 1.8 mmol) and 2-(3-bromomethyl-indazol-1-yl)-benzonitrile (Intermediate 1) (676.18 mg, 2.16 mmol) were converted to the title compound (670 mg, 72.9%) which was obtained as light yellow solid. LC-MS: 509 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409888B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-9a63469407e14ba583b80b87299592f2 |
| Source note | uspto-grants-2016_08 |