Trifluoroacetic acid → (E)-4-(3-chlorophenyl)-8-(2-phenylethynyl)-1H-benzo[b][1,4]diazepin-2(3H)-one

HRID 1062128Notes

Reaction equation

HRID 1062128 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH2:22])(C)(C)C.[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2OC(C)(C)O[C:33](=[O:39])[CH:32]=2)[CH:28]=[CH:29][CH:30]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[CH2:32][C:33](=[O:39])[NH:22][C:9]3[CH:10]=[C:11]([C:14]#[C:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11404065(2-Amino-4-phenylethynyl-phenyl)-carbamic acid tert-butyl esterHCID 222246906-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one

Product 1

HCID 9864190(E)-4-(3-chlorophenyl)-8-(2-phenylethynyl)-1H-benzo[b][1,4]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from (2-amino-4-phenylethynyl-phenyl)-carbamic acid tert.-butyl ester (Example G2) and 6-(3-chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one (Example J6) 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 an orange solid (155 mg).

Sources & evidence

ORD record
ord-be9e404222344138802d9e99edcf9dec
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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