Acetoxyacetyl chloride → HCID 66780417, compound

HRID 1958054Notes

Reaction equation

HRID 1958054 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14]1[N:15]=[C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[S:17][C:18]=1[C:19]([NH2:21])=[O:20].[C:28]([O:31][CH2:32][C:33](Cl)=O)(=[O:30])[CH3:29]>O1CCCC1>[C:28]([O:31][CH2:32][C:33]1[N:13]([CH2:12][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:9])([F:10])[F:11])[C:2]=2[CH3:1])[C:14]2[N:15]=[C:16]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[S:17][C:18]=2[C:19](=[O:20])[N:21]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 66779840HCID 66779840, compound

Product 1

HCID 66780417HCID 66780417, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-({[2-methyl-3-(trifluoromethyl)phenyl]methyl}amino)-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (300 mg, 0.749 mmol), 2-chloro-2-oxoethyl acetate (0.201 mL, 1.873 mmol) in Tetrahydrofuran (THF) (6 mL) was charged into a sealed tube under 0 C. The mixture was warmed up to RT gradually. The reaction was stirred at RT for overnight. The mixture was partitioned between DCM and NaCl, the organic layer was concentrated and the residue was purified on silica column (5% MeOH/DCM) to give product 80 mg (˜20%).

Workup

  1. customThe mixture was partitioned between DCM and NaCl
  2. concentrationthe organic layer was concentrated
  3. customthe residue was purified on silica column (5% MeOH/DCM)

Sources & evidence

ORD record
ord-3046108bf0b1413c97ea82edb650c9d0
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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