Neophyl chloride → 4-methyl-2-[1-(2-methyl-2-phenyl-propyl)-1H-pyrazol-3-yl]-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amide

HRID 1879199Notes

Reaction equation

HRID 1879199 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.Cl[CH2:23][C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:26])[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][C:24]([CH3:26])([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:25])[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 68191Neophyl chlorideHCID 866455594-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide

Product 1

HCID 594895324-methyl-2-[1-(2-methyl-2-phenyl-propyl)-1H-pyrazol-3-yl]-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amideYield 20%

Procedure

The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide and (2-chloro-1,1-dimethyl-ethyl)benzene as described in Example 49 and isolated as a white solid, (0.025 mg, 20% yield). 1H NMR (400 MHz, CDCl3) δ 8.65 (bs, 1H), 8.57 (d, J=4 Hz, 1H), 7.78 (d, J=8 Hz, 1H), 7.23-7.49 (m, 6H) 6.69 (d, J=2 Hz, 1H), 6.63 (d, J=2 Hz, 1H), 6.12-6.18 (bm, 1H), 4.64 (d, J=4 Hz, 2H), 4.28 (s, 2H), 2.75 (s; 3H), 1.40 (s, 6H); MS (M+H)+=432.2; Rt=1.39 min; HRMS (M+H)+=432.19.

Workup

  1. customisolated as a white solid, (0.025 mg, 20% yield)

Sources & evidence

ORD record
ord-88a29405040f443e8a56b56f74ae79ad
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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