Ethanol → HCID 86721222, compound

HRID 1750381Notes

Reaction equation

HRID 1750381 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.[NH2:22][C:23](=[S:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26].[CH3:30]CO>>[C:18]([N:8]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:5]([C:3]2[N:22]=[C:23]([CH2:24][C:25]([O:27][CH2:28][CH3:30])=[O:26])[S:29][CH:2]=2)[CH:6]=[N:7]1)([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 3035269Propanoic acid, 3-amino-3-thioxo-, methyl esterHCID 86721221HCID 86721221, compound

Product 1

HCID 86721222HCID 86721222, compound

Procedure

A solution of the compound (107 mg, 0.30 mmol) obtained in step 5 and methyl 3-amino-3-thioxopropanoate (48.7 mg, 0.37 mmol) in EtOH (3 mL) was stirred at 90° C. for 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 5→80% ethyl acetate/hexane) to give a crude product ethyl 2-(4-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-2-yl)acetate as a colorless oil, which was used for the next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH-silica gel column chromatography (solvent gradient; 5→80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f99cb122a7d41e3944693ae99c64097
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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