Methanol → HCID 9885954, compound

HRID 275759Notes

Reaction equation

CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=O.[CH3:22][NH:23][C:24](=[O:31])[CH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CO.[H-].[Na+]>CN(C)C=O.O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:4]2[CH:3]=[C:25]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[C:24](=[O:31])[N:23]([CH3:22])[C:5]=2[C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 3-dimethylamino-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one (2.53 g), N-methyl thiazol-2-ylacetamide (1.70 g) and methanol (0.73 cm3) in dry dimethylformamide (20 cm3) was added via cannula at room temperature to a stirred suspension of sodium hydride (55% in oil; 0.80 g) in dry dimethylformamide (10 cm3) under nitrogen. The mixture was stirred at 40° C. for 18 hours, then poured into water (200 cm3). The resulting yellow precipitate was collected and recrystallised from ethyl acetate to give 3-(4-methoxyphenyl)-1-methyl-5-(thiazol-2-yl)-1H-[2,4′]bipyridinyl-6-one as a yellow powder (2.18 g; 62%) m.p. 224-225° C. (EtOAc). Found: C, 66.9; H, 4.45; N, 11.2. C12H17N3O2S requires C, 67.2; H, 4.6; N, 11.2%. δH (360 MHz; CDCl3) 3.50 (3 H, s, NCH3), 3.74 (3 H, s, OCH3), 6.70 (2 H, d, J 9, methoxyphenyl H-2), 6.93 (2 H, d, J 9, methoxyphenyl H-3), 7.15 (2 H, d, J 6, pyridyl H-3), 7.50 (1 H, d, J 3, thiazolyl H-5), 7.96 (1 H, d, J 3, thiazolyl H-4), 8.64 (2 H, d, J 6, pyridyl H-2) and 8.72 (1 H, s, pyridone H-4); m/z (ESP+) 376 (MH+; 100%).

Workup

customThe resulting yellow precipitate was collected
customrecrystallised from ethyl acetate

Sources & evidence

ORD record: ord-be845e31d740434299c6455cebf07d50
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352994B2

Reaction notes

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