Methanol → HCID 178488507, compound

HRID 275767Notes

Reaction equation

COC(=O)[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[CH:5]N(C)C.[CH3:18][NH:19][C:20](=[O:28])[CH2:21][C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1.[CH3:29][OH:30].[H-].[Na+]>CN(C)C=O>[OH:30][C:29]1[N:19]([CH3:18])[C:20](=[O:28])[C:21]([C:22]2[S:23][CH:24]=[C:25]([CH3:27])[N:26]=2)=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl-3-dimethylamino-2-(4-methoxyphenyl)propenoate (1.6 g), N-methyl-2-(4-methylthiazol-2-yl)acetamide (1 g) and methanol (0.28 cm3) were dissolved in N,N-dimethylformamide (30 cm3) and cooled to 0° C. under N2. Sodium hydride (60% suspension in oil, 0.28 g) was added and the mixture heated at 80° C. for 18 h. The mixture was cooled, partitioned between ethyl acetate (200 cm3) and water (200 cm3). The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate (3×100 cm3) which was dried (MgSO4) ) and evaporated. The crude solid was recrystaolised from e thyl acetate/ether to yield pure 6-hydroxy-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one (0.3 g). δH (250 MHz; CDCl3); 2.37 (3H, s), 3.48 (3H, s), 3.83 (3 H, s), 6.37 (1H, s), 6.92 (2H, d, J 8. 7 Hz), 7.33 (1H, s) and 7.53 (2H, d, J 8.7 Hz); m/z (ESP+) 329 (MH+).

Workup

temperaturethe mixture heated at 80° C. for 18 h
temperatureThe mixture was cooled
custompartitioned between ethyl acetate (200 cm3) and water (200 cm3)
extractionextracted with ethyl acetate (3×100 cm3) which
dry with materialwas dried (MgSO4) ) and
customevaporated

Sources & evidence

ORD record: ord-bc195e8e375a44bb9a1087dafb832fed
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352994B2

Reaction notes

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