4,5-Dibromothenoic acid → N-{2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

HRID 2392009Notes

Reaction equation

HRID 2392009 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[S:5][C:6]=1Br.[NH2:11][CH:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([F:31])([F:30])[F:29])[CH2:13][NH:14]C(=O)OC(C)(C)C.[NH2:32][CH:33](CC1C=CC=CC=1)[CH2:34][CH2:35][NH:36][C:37](=O)OC(C)(C)C>>[NH2:14][CH2:13][CH:12]([NH:11][C:8]([C:4]1[S:5][CH:6]=[C:2]([C:35]2[N:36]([CH3:37])[N:32]=[CH:33][CH:34]=2)[CH:3]=1)=[O:10])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([F:29])([F:30])[F:31]

Participants

4

Reactant 3

HCID 806114,5-Dibromothenoic acidHCID 16244624tert-butyl N-{2-amino-2-[2-(trifluoromethyl)phenyl]ethyl}carbamateHCID 597772381,1-Dimethylethyl (3-amino-4-phenylbutyl)carbamate

Product 1

HCID 24995937N-{2-amino-1-[2-(trifluoromethyl)phenyl]ethyl}-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Procedure

The title compound was prepared as a white solid according to the procedure of Example 20, except substituting 4-bromo-2-thiophenecarboxylic acid (104 mg, 0.5 mmol) for 4,5-dibromo-2-thiophenecarboxylic acid and substituting 1,1-dimethylethyl {2-amino-2-[2-(trifluoromethyl)phenyl]ethyl}carbamate (152 mg, 0.5 mmol) [prepared according to the procedure of Preparation 16] for 1,1-dimethylethyl (3-amino-4-phenylbutyl)carbamate: LC-MS (ES) m/z 395 (M+H)+, 1H NMR (400 MHz, MeOD) δ ppm 3.36-3.39 (m, 1H) 3.46-3.53 (m, 1H) 3.98 (s, 3H) 5.86-5.91 (m, 1H) 6.48 (s, 1H) 7.51 (d, J=2.02 Hz, 1H) 7.60 (s, 1H) 7.76 (s, 1H) 7.83 (d, J=8.08 Hz, 2H) 7.94 (s, 1H) 8.05 (s, 1H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-92637ef2f2124e0cb8a01f065d75cef5
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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