Dimethylformamide dimethyl acetal → HCID 68801242, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][S:11]3)=[CH:4][C:3]=1[O:19][CH3:20].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>>[CH3:23][N:24]([CH3:26])[CH:25]=[CH:17][C:16]([C:15]1[N:14]2[C:10]([S:11][CH:12]=[CH:13]2)=[N:9][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:19][CH3:20])[CH:4]=1)=[O:18]Participants
3
Procedure
A 100 ml round bottom flask was charged with the 1-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]ethanone (1.12 g, 3.86 mmol) and dimethylformamide dimethylacetal (25 ml). The mixture was refluxed for 20 hours and then cooled to room temperature. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (ethyl acetate), giving a pale yellow solid (1.138 g, 85%). 400 MHz 1H NMR (DMSO-d6) δ: 8.39 (d, J=4.7 Hz, 1H), 7.62 (d, J=12.5 Hz, 1H), 7.45-7.40 (m, 2H), 7.31 (dd, J=11.3, 8.2 Hz, 1H), 7.20 (ddd, J=8.2, 4.3, 2.0 Hz, 1H), 5.10 (d, J=12.5 Hz, 1H), 3.87 (s, 3H), 3.06 (br. s, 3H), 2.49 (br. s, 3H). LCMS: 346 [M+H].
Workup
- temperatureThe mixture was refluxed for 20 hours