1-(Bromomethyl)-4-(trifluoromethyl)benzene → 4-methyl-2-[1-(4-trifluoromethyl-benzyl)-1H-pyrazol-3-yl]-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amide

HRID 1879192Notes

Reaction equation

HRID 1879192 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]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][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:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=4)[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 866455594-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide

Product 1

HCID 249518574-methyl-2-[1-(4-trifluoromethyl-benzyl)-1H-pyrazol-3-yl]-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amide

Procedure

The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide and bromomethyl-4-trifluoromethyl-benzene as described in Example 49 and isolated as yellow solid (0.075 g, 50% yield). 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.56 (d, J=4 Hz, 2H), 7.70 (d, J=4 Hz, 1H), 7.61 (d, J=8 Hz, 2H), 7.44 (d, J=4 Hz, 1H), 7.26-7.36 (m, 3H), 6.88 (d, J=2 Hz, 1H), 6.13 (t, J=5 Hz, 1H), 5.41 (s, 2H), 4.63 (d, J=8 Hz, 2H), 2.75 (s, 3H); MS (M+H)+=458.1; Rt=1.35 min; HRMS (M+H)+=458.13.

Sources & evidence

ORD record
ord-0684499303ca4408b8db88675e4b410c
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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