1-Bromo-2-phenylpropane → 4-methyl-2-[1-(2-phenyl-propyl)-1H-pyrazol-3-yl]-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][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:25]>>[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][CH:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH3:25])[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 (2-bromo-1-methyl-ethyl)benzene as described in Example 49 and isolated as a white solid (0.120 mg, 45% yield). 1H NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 8.55 (d, J=4 Hz, 1H), 7.71 (d, J=8 Hz, 1H), 7.18-7.33 (m, 4H), 7.12 (d, J=8 Hz, 2H), 7.03 (d, J=2 Hz, 1H), 6.67 (d, J=2 Hz, 1H), 6.16-6.24 (m, 1H), 4.63 (d, J=4 Hz, 2H), 4.18-4.31 (m, 2H), 3.34-3.44 (m, 1H), 2.74 (s, 3H), 1.29 (d, J=4 Hz, 3H); MS (M+H)+=418.2; Rt=1.31 min; HRMS (M+H)+=418.17.
Sources & evidence
- ORD record
- ord-9f425ce451364f649a997a13bfb833a1
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314138B2
Reaction notes
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