2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → HCID 24983663, compound

HRID 1887288Notes

Reaction equation

HRID 1887288 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[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]=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[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 178516128HCID 178516128, compound

Product 1

HCID 24983663HCID 24983663, compoundYield 9%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-hydroxy-4-(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 9% yield: mp 197-198° C.; 1H NMR (300 MHz, CDCl3) δ 8.93 (d, J=7.8 Hz, 1H), 7.39-7.25 (m, 5H), 7.00 (d, J=0.6 Hz, 1H), 6.57-6.54 (m, 1H), 6.17 (s, 1H), 4.59 (d, J=5.7 Hz, 2H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 159.3, 152.4, 141.0, 137.5, 133.1, 128.8, 127.9, 127.8, 124.1, 119.1, 103.0, 44.2, 17.3; MS (ES+) m/z 394.2 (M+1).

Sources & evidence

ORD record
ord-485209743f65402eaed3381bc2844f56
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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