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

HRID 859547Notes

Reaction equation

HRID 859547 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][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[NH2:23])(C)(C)C.C(O[C:28](=[O:43])[CH2:29][C:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[CH:41]=[N:40][N:39]=[N:38]2)[CH:32]=1)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]#[C:14][C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[C:30]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([N:37]5[CH:41]=[N:40][N:39]=[N:38]5)[CH:32]=4)[CH2:29][C:28](=[O:43])[NH:23][C:9]=3[CH:10]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69486641[2-Amino-4-(4-fluoro-phenylethynyl)-phenyl]-carbamic acid tert-butyl esterHCID 695927913-Oxo-3-(3-tetrazol-1-yl-phenyl)-propionic acid ethyl ester

Product 1

HCID 98451278-(4-Fluoro-phenylethynyl)-4-(3-tetrazol-1-yl-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from [2-amino-4-(4-fluoro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester (Example G33) and 3-oxo-3-(3-tetrazol-1-yl-phenyl)-propionic acid ethyl ester (Example H15) 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 beige powder (5.5 mg).

Sources & evidence

ORD record
ord-b68747766c3343d6829ef30b248f3956
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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