HCID 86721282, compound → HCID 86721286, compound

HRID 1750444Notes

Reaction equation

HRID 1750444 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]2[S:19][CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.CO.[C].[Pd]>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[C:8]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 86721282HCID 86721282, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86721286HCID 86721286, compoundYield 89.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of (E)-3-(2-(1-(tert-butyl)-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acrylic acid (70 mg, 0.18 mmol) and 10% palladium carbon (19.43 mg, 0.18 mmol) in THF (2 mL) and methanol (2 mL) was stirred under 1 atm hydrogen atmosphere at room temperature for 14 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was crystallized from diethyl ether to give 3-(2-(1-(tert-butyl)-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-4-yl)propanoic acid (62.0 mg, 0.161 mmol, 88%) as a white powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f1eb57bb8f6a4a2e954ebc74b316f48c
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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