Trifluoroacetic acid → N-(4-amino-1-phenyl-1H-pyrazol-3-yl)-4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzamide

HRID 913254Notes

Reaction equation

HRID 913254 reaction equation
[F:1][C:2]([F:44])([C:31]1[O:32][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:42][CH3:43])=[N:34][N:35]=1)[C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[C:14]([NH:15]C(=O)OC(C)(C)C)=[CH:13][N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:11]=2)=[O:8])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:15][C:14]1[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:44])[C:31]3[O:32][C:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[N:34][N:35]=3)=[CH:30][CH:29]=2)=[N:11][N:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57541231tert-butyl {3-[(4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate

Product 1

HCID 16738871N-(4-amino-1-phenyl-1H-pyrazol-3-yl)-4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {3-[(4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate (10 mg) in methylene chloride (2 mL) was added trifluoroacetic acid (1 mL) and the solution was stirred at ambient temperature for 16 hours. The reaction was evaporated to dryness to give N-(4-amino-1-phenyl-1H-pyrazol-3-yl)-4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzamide as a yellowish solid. 1H NMR (CD3OD) δ 8.45 (s, 1H), 8.23 (d, J=8.21 Hz, 2H), 7.93 (m, 3H), 7.79 (d, J=7.62 Hz, 2H), 7.64 (m, 1H), 7.52 (t, J=7.62 Hz, 2H), 7.37 (t, J=7.62 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.14 (t, J=7.62 Hz, 1H), 3.96 (s, 3H); ESIMS calcd 503.2 (M++H), found 503.1 (M++H).

Workup

  1. customThe reaction was evaporated to dryness

Sources & evidence

ORD record
ord-3eb2c33ad22340f989242c7a86edbaec
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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