4-(Bromomethyl)benzonitrile → HCID 24951497, compound

HRID 1879186Notes

Reaction equation

HRID 1879186 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:31]=[CH:30][C:27]([C:28]#[N:29])=[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:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 866455594-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide

Product 1

HCID 24951497HCID 24951497, compound

Procedure

The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide and 4-bromomethyl-benzonitrile as described in Example 49 and isolated as a white solid (0.065 g, 46% 1H NMR (400 CDCl3) δ 3.60 (s, 1H), 8.55-8.57 (m, 1H), 7.71 (d, J=8 Hz, 1H), 7.64 (d, J=8 Hz, 2H), 7.46 (s, 1H), 7.26-7.31 (m, 3H), 6.90 (d, J=4 Hz, 1H), 6.11-6.16 (m, 1H), 5.41 (s, 2H), 4.63 (d, J=8 Hz, 2H), 2.75 (s, 3H); MS (M+H)+=415.2; Rt=1.15 min; HRMS (M+H)+=415.14.

Workup

  1. customisolated as a white solid (0.065 g, 46% 1H NMR (400 CDCl3) δ 3.60 (s, 1H), 8.55-8.57 (m, 1H), 7.71 (d, J=8 Hz, 1H), 7.64 (d, J=8 Hz, 2H), 7.46 (s, 1H), 7.26-7.31 (m, 3H), 6.90 (d, J=4 Hz, 1H), 6.11-6.16 (m, 1H), 5.41 (s, 2H), 4.63 (d, J=8 Hz, 2H), 2.75 (s, 3H)

Sources & evidence

ORD record
ord-80d9d7b51b084ef7b308b447cef98b46
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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