2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → HCID 24985272, compound

HRID 1887294Notes

Reaction equation

HRID 1887294 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][N:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30](Br)=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30]([N:16]2[CH:15]=[CH:14][C:4]([C:5](=[O:6])[NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:3][C:2]2=[O:1])=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178521923HCID 178521923, compound

Product 1

HCID 24985272HCID 24985272, compoundYield 20%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-hydroxy-N-phenylisonicotinamide in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 20% yield: mp 243-245° C. (hexane/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 10.53 (s, 1H), 8.88 (t, J=5.8 Hz, 1H), 8.83 (d, J=7.6 Hz, 1H), 7.72 (d, J=7.6 Hz, 2H), 7.36-7.19 (m, 8H), 7.10 (t, J=7.3 Hz, 1H), 6.98 (dd, J=7.6, 1.8 Hz, 1H), 4.40 (d, J=5.8 Hz, 2H), 2.59 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.0, 161.7, 160.2, 153.5, 150.7, 139.8, 132.0, 129.1, 128.7, 127.7, 127.2, 124.7, 124.6, 123.6, 121.0, 119.5, 107.0, 106.1, 43.2, 17.5; (ES+) m/z 445.1 (M+1).

Sources & evidence

ORD record
ord-1e46900325064432a2ac02d12087a743
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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