Ethyl 4-chloroacetoacetate → HCID 86721247, compound

HRID 1750403Notes

Reaction equation

HRID 1750403 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18](=[S:20])[NH2:19])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][C:23](=O)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]2[S:20][CH:22]=[C:23]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:19]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 86721245HCID 86721245, compound

Product 1

HCID 86721247HCID 86721247, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (700 mg, 2.42 mmol) obtained in step 11 and ethyl 4-chloroacetoacetate (0.392 mL, 2.90 mmol) in ethanol (5 mL) was stirred at 80° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diethyl ether and hexane to give ethyl 2-(2-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate (920 mg, 2.33 mmol, 95%) as a pale-yellow powder.

Workup

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

Sources & evidence

ORD record
ord-3892179484aa401188572b699495ca50
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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