4-Fluorobenzyl bromide → HCID 24801154, compound

HRID 883155Notes

Reaction equation

HRID 883155 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1>>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH:18]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:17]2=[O:22])=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 24801154HCID 24801154, compoundYield 61%

Procedure

Following the procedure as described in Example 2, making variation as required to use N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide to react with 1-(bromomethyl)-4-fluorobenzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 61% yield: mp 154-155° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.34-7.21 (m, 5H), 7.12-7.07 (m, 2H), 6.99-6.88 (m, 2H), 6.16 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H), 4.29-4.16 (m, 1H), 3.97-3.82 (m, 1H), 3.39-3.25 (m, 1H), 2.82-2.66 (m, 2H), 2.61 (s, 3H), 2.06-1.91 (m, 1H), 1.89-1.69 (m, 2H), 1.57-1.41 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.9, 162.7, 161.6, 156.9, 151.9, 138.0, 134.6, 130.6, 128.8, 127.9, 127.6, 119.6, 115.3, 48.0, 44.1, 44.0, 36.7, 24.8, 21.2, 17.4; MS (ES+) m/z 438.2 (M+1).

Sources & evidence

ORD record
ord-d980aef83dd04b4bbc924cb2714d03ce
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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