Dimethylformamide dimethyl acetal → HCID 68801242, compound

HRID 1783823Notes

Reaction equation

HRID 1783823 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

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57433636HCID 57433636, compound

Product 1

HCID 68801242HCID 68801242, compoundYield 85%

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

  1. temperatureThe mixture was refluxed for 20 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8a740da2163041bda748483667e07a22
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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