2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → HCID 24983661, compound

HRID 1887286Notes

Reaction equation

HRID 1887286 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25](Br)=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([N:3]2[CH:4]=[C:5]([C:8]([F:9])([F:11])[F:10])[CH:6]=[CH:7][C:2]2=[O:1])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178516044HCID 178516044, compound

Product 1

HCID 24983661HCID 24983661, compoundYield 60%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-hydroxy-5-(trifluoromethyl)pyridine 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 white solid in 60% yield: mp 148-149° C.; 1H NMR (300 MHz, CDCl3) δ 9.19 (br s, 1H), 7.53 (dd, J=9.6, 2.7 Hz, 1H), 7.37-7.25 (m, 5H), 6.78 (d, J=9.6 Hz, 1H), 6.27 (t, J=5.7 Hz, 1H), 4.58 (d, J=5.7 Hz, 2H), 2.69 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 159.6, 152.4, 151.9, 137.6, 135.2, 131.1, 128.8, 127.9, 124.6, 124.5, 122.1, 121.1, 111.8, 44.2, 17.2; MS (ES+) m/z 394.2 (M+1).

Sources & evidence

ORD record
ord-052d7813277a48e89322146f889fcb80
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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