Trifluoroacetic acid → 8-(6-Benzyloxy-pyridin-3-yl)-4-(3-chloro-thiophen-2-yl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 859513Notes

Reaction equation

HRID 859513 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:19]=2)=[CH:10][C:9]=1[NH:28][C:29](=[O:39])[CH2:30][C:31]([C:33]1[S:34][CH:35]=[CH:36][C:37]=1[Cl:38])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:21]([O:20][C:17]1[N:16]=[CH:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[C:31]([C:33]4[S:34][CH:35]=[CH:36][C:37]=4[Cl:38])[CH2:30][C:29](=[O:39])[NH:28][C:9]=3[CH:10]=2)=[CH:19][CH:18]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588014{4-(6-Benzyloxy-pyridin-3-yl)-2-[3-(3-chloro-thiophen-2-yl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl ester

Product 1

HCID 222245588-(6-Benzyloxy-pyridin-3-yl)-4-(3-chloro-thiophen-2-yl)-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from {4-(6-benzyloxy-pyridin-3-yl)-2-[3-(3-chloro-thiophen-2-yl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl ester (Example K26) (172 mg, 0.3 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a yellow solid (38 mg).

Sources & evidence

ORD record
ord-2ba96e31db1e422b9e57f72c8595dbde
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

Loading…