1-(2-Bromoethyl)-4-methoxybenzene → 2-{1-[2-(4-methoxy-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)amide

HRID 1879198Notes

Reaction equation

HRID 1879198 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][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=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][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 866455594-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide

Product 1

HCID 249564902-{1-[2-(4-methoxy-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-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 1-(2-bromo-ethyl)-4-methoxy-benzene as described in Example 49 and isolated as a white solid (0.030 mg, 21% yield). 1H NMR (400 MHz, CDCl3) δ 8.55-8.63 (bm, 2H), 7.72 (d, J=8 Hz, 1H), 7.28-7.33 (m, 1H), 7.15 (d, J=2 Hz, 1H), 6.97 (d, J=8 Hz, 2H), 6.80 (d, J=8 Hz, 2H), 6.72 (d, J=2 Hz, 1H), 6.12-6.19 (m, 1H), 4.64 (d, J=8 Hz, 2H), 4.33 (t, J=8 Hz, 2H), 3.77 (s, 3H), 3.12 (t, J=8 Hz, 3H), 2.76 (s, 3H); MS (M+H)+=433.9; Rt=1.25 min; HRMS (M+H)+=434.16.

Sources & evidence

ORD record
ord-336cb2f6cc734998bb6b4d864b3d7302
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…