Trifluoroacetic acid → 4-(3-Chloro-phenyl)-8-phenyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1635362Notes

Reaction equation

HRID 1635362 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:9]=1[NH2:20])(C)(C)C.[Cl:22][C:23]1[CH:24]=[C:25]([C:29]2OC(C)(C)O[C:31](=[O:37])[CH:30]=2)[CH:26]=[CH:27][CH:28]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([C:29]2[CH2:30][C:31](=[O:37])[NH:20][C:9]3[CH:10]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 222246906-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 57717454N-(3-Amino[1,1'-biphenyl]-4-yl)-carbamic Acid tert-Butyl Ester

Product 1

HCID 222249324-(3-Chloro-phenyl)-8-phenyl-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from (3-amino-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G9) (284 mg, 1.0 mmol) and 6-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one (Example J6) (358 mg, 1.2 mmol) according to the general procedure K. The obtained material (339 mg) was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a yellow solid (188 mg).

Sources & evidence

ORD record
ord-312934e1155a4685bfcb96b4b9521686
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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