3,5-Difluorobenzyl bromide → 2-[1-(3,5-difluoro-benzyl)-1H-pyrazol-3-yl]-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[NH:17][N:18]=[CH:19][CH:20]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1.Br[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:23][C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=4)[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1Participants
3
Procedure
The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide and 1-bromomethyl-3,5-difluoro-benzene as described in Example 49 and isolated as a white solid (0.071 mg, 51% yield). 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.56 (d, J=4 Hz, 1H), 7.71 (d, J=8 Hz, 1H), 7.45 (d, J=2 Hz, 1H), 7.28-7.34 (m, 1H), 6.89 (d, J=2 Hz, 1H), 6.70-6.79 (m, 3H), 6.12-6.18 (m, 1H), 5.32 (s, 2H), 4.63 (d, J=8 Hz, 2H), 2.75 (s, 3H); MS (M+H)+=425.9; Rt=1.25 min; HRMS (M+H)+=426.12.
Sources & evidence
- ORD record
- ord-3b1dd3bc87864f33990b80628bf3c3a3
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314138B2
Reaction notes
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