Trifluoroacetic acid → 8-Phenyl-4-thiophen-2-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1635360Notes

Reaction equation

HRID 1635360 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.CC1(C)O[C:27](=[O:29])[CH:26]=[C:25]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)O1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:14]1([C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[C:25]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[CH2:26][C:27](=[O:29])[NH:20][C:9]=3[CH:10]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 222247082,2-Dimethyl-6-thiophen-2-yl-[1,3]dioxin-4-oneHCID 57717454N-(3-Amino[1,1'-biphenyl]-4-yl)-carbamic Acid tert-Butyl Ester

Product 1

HCID 222247458-Phenyl-4-thiophen-2-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-oneYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from (3-amino-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G9) (69 mg, 0.243 mmol) and 2,2-dimethyl-6-thiophen-2-yl-[1,3]dioxin-4-one (Example J1) (54 mg, 0.257 mmol) according to the general procedure K. The obtained material was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a brown solid (46 mg).

Sources & evidence

ORD record
ord-5697b732c6404fa58e97c9f02d046ca9
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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