Ammonium Chloride → 2-Propionyl-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole

HRID 230036

Reaction equation

HRID 230036 reaction equation
Br[C:2]1[S:6][C:5]2=[C:7]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:8]=[CH:9][N:4]2[C:3]=1[CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20].C([Mg]Br)C.CN(OC)[C:31](=[O:34])[CH2:32][CH3:33].[Cl-].[NH4+]>O1CCCC1>[C:31]([C:2]1[S:6][C:5]2=[C:7]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:8]=[CH:9][N:4]2[C:3]=1[CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])(=[O:34])[CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 11344007N-Methoxy-N-methylpropionamideHCID 688224232-Bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 688215852-Propionyl-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazoleYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.14 g of 2-bromo-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole in 36 ml of tetrahydrofuran under an argon atmosphere was cooled to −60° C., 13.3 ml of a 0.89 M tetrahydrofuran solution of ethylmagnesium bromide was added thereto, and the mixture was stirred for one hr. N-Methyl-N-methoxypropionamide (1.71 g) was added thereto at −30° C., and the mixture was stirred at room temperature for 12 hr. A 20% aqueous ammonium chloride solution was added to stop the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and saturated brine in that order and was then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (3 to 6% methanol/methylene chloride) to give 3.88 g of 2-propionyl-7-(pyridin-3-yl)triethylsilyloxymethylimidazo[5,1-b]thiazole.

Workup

  1. stirringat −30° C., and the mixture was stirred at room temperature for 12 hr
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous sodium bicarbonate solution and saturated brine in that order
  5. dry with materialwas then dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by column chromatography on silica gel (3 to 6% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d66fc189776f456b85011a271271c3ef
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Linked notes

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