Water → 2-Bromo-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamide

HRID 1967838Notes

Reaction equation

HRID 1967838 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[S:13][C:12]([NH2:14])=[N:11][C:10]=2[C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:27][CH2:28][C:29](Br)=[O:30].O>CN(C1C=CN=CC=1)C.C1COCC1>[Br:27][CH2:28][C:29]([NH:14][C:12]1[S:13][C:9]([C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[O:8])=[C:10]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:11]=1)=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 866124682-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole

Product 1

HCID 231445052-Bromo-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamideYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Compound 454 (1.39 g, 5.00 mmol), triethylamine (3.06 mL, 22.0 mmol) and DMAP (61.0 mg, 0.500 mmol) were suspended in THF (30 mL), and bromoacetyl bromide (1.64 mL, 20.0 mmol) was added dropwise thereto at 0° C., followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1), followed by reslurrying with diethyl ether to afford the entitled Compound 531 (1.59 g, 80%) as a pale brown solid.

Workup

  1. customat 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-a251368f679e4a549d9786c75917d001
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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