N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide → N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

HRID 883142Notes

Reaction equation

HRID 883142 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21]Br)=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C1SC(NC(=O)CCCBr)=NC=1C)=O)C1C=CC=CC=1>>[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:23])=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86638730N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamideHCID 86638732N-benzyl-2-(5-bromopentanamido)-4-methylthiazole-5-carboxamide

Product 1

HCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamideYield 35%

Procedure

Following the procedure as described in Example 1, making variations as required to use N-benzyl-2-(5-bromopentanamido)-4-methylthiazole-5-carboxamide in replace of N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 35% yield: mp 175-176° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.33-7.25 (m, 5H), 5.96 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.13 (t, J=6.0 Hz, 2H), 2.66 (t, J=6.8 Hz, 2H), 2.64 (s, 3H), 2.02-1.87 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 169.8, 162.7, 156.9, 152.0, 138.0, 128.8, 127.9, 127.6, 119.4, 48.0, 44.0, 32.7, 22.5, 20.2, 17.4; MS (ES+) m/z 330.6 (M+1).

Sources & evidence

ORD record
ord-c03e522fb7fe41668ee9b48e85c35d49
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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