Ethyl 4-chloroacetoacetate → ethyl 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate

HRID 1750343Notes

Reaction equation

HRID 1750343 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17](=[S:19])[NH2:18])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:21][C:22](=O)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:19][CH:21]=[C:22]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:18]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 867211801-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide

Product 1

HCID 86721181ethyl 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetateYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (2.90 g, 10.46 mmol) obtained in step 4 and ethyl 4-chloroacetoacetate (1.554 mL, 11.50 mmol) in ethanol (30 mL) was stirred at 80° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate and hexane to give ethyl 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetate (3.96 g, 10.22 mmol, 98%) as a pale-yellow powder.

Workup

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

Sources & evidence

ORD record
ord-ae005e53108e4cec84136c1075ee1ee3
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

Loading…