Ethyl 4-chloroacetoacetate → HCID 86721261, compound

HRID 1750416Notes

Reaction equation

HRID 1750416 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19](=[S:21])[NH2:20])[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:23][C:24](=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(O)C>[CH:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)=[C:10]([C:19]3[S:21][CH:23]=[C:24]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:20]=3)[CH:9]=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 86721260HCID 86721260, compound

Product 1

HCID 86721261HCID 86721261, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (236 mg, 0.78 mmol) obtained in step 2 and ethyl 4-chloroacetoacetate (0.126 ml, 0.93 mmol) in ethanol (4 mL) was stirred at 90° C. for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from hexane to give ethyl 2-(2-(1-cyclohexyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate (269 mg, 0.651 mmol, 84%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-66cf72ed6b2d4d9bb54e4c006805c362
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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