2(1H)-Pyridinone, 3-(trifluoromethyl)- → HCID 24983662, compound

HRID 1887287Notes

Reaction equation

HRID 1887287 reaction equation
[OH:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][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][CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[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 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24983662HCID 24983662, compoundYield 37%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 2-hydroxy-3-(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 37% yield: mp 203-204° C.; 1H NMR (300 MHz, CDCl3) δ 9.01 (d, J=7.2 Hz, 1H), 7.87 (d, J=7.2 Hz, 1H), 7.36-7.23 (m, 5H), 6.53 (t, J=7.2 Hz, 1H), 6.10 (s, 1H), 4.57 (d, J=5.4 Hz, 2H), 2.69 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.7, 156.6, 152.2, 152.1, 139.3, 139.2, 137.4, 135.1, 128.9, 128.8, 127.8, 123.8, 121.9, 106.0, 44.2, 17.2; MS (ES+) m/z 394.2 (M+1).

Sources & evidence

ORD record
ord-505e9f13949a40f4aca217ece5911f55
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…