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

HRID 859489Notes

Reaction equation

HRID 859489 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.CC1(C)O[C:29](=[O:31])[CH:28]=[C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34](OC(F)(F)F)[CH:33]=2)O1.C(O)([C:46]([F:49])([F:48])[F:47])=O>C(Cl)Cl>[C:16]1([C:15]#[C:14][C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[C:27]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:46]([F:49])([F:48])[F:47])[CH:33]=4)[CH2:28][C:29](=[O:31])[NH:22][C:9]=3[CH:10]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11404065(2-Amino-4-phenylethynyl-phenyl)-carbamic acid tert-butyl esterHCID 222247282,2-Dimethyl-6-(3-trifluoromethoxy-phenyl)-[1,3]dioxin-4-one

Product 1

HCID 222245838-(2-phenylethynyl)-4-(3-(trifluoromethyl)phenyl)-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 2,2-dimethyl-6-(3-trifluoromethoxy-phenyl)-[1,3]dioxin-4-one (Example J8) 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 yellow solid (157 mg).

Sources & evidence

ORD record
ord-69bc13e40b814d64b9f2a5870f31546f
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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