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

HRID 1481897Notes

Reaction equation

HRID 1481897 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16]C2C3C(=C(Br)C=CC=3)C=CC=2OC)[C:12]2[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)N[C@@H]1C(=O)NC2C=CC=CC=2NC1)(C)(C)C.BrC[C:57]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[N:59]([C:66]2[CH:73]=[CH:72][CH:71]=[CH:70][C:67]=2[C:68]#[N:69])[N:58]=1>>[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][C:57]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[N:59]([C:66]3[CH:73]=[CH:72][CH:71]=[CH:70][C:67]=3[C:68]#[N:69])[N:58]=2)[C:12]2[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=2[NH:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate2×HCID 900376452-(3-Bromomethyl-indazol-1-yl)-benzonitrile2×HCID 90221057[(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 ester2×

Product 1

HCID 90221209{(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 esterYield 72.9%

Procedure

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).

Sources & evidence

ORD record
ord-9a63469407e14ba583b80b87299592f2
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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