HCID 86721284, compound → HCID 86721283, compound

HRID 1750442Notes

Reaction equation

HRID 1750442 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]([NH:27][CH2:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[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]([CH2:23][CH2:24][C:25]([NH:27][CH2:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86721284HCID 86721284, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86721283HCID 86721283, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of (2E)-3-{2-[1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)prop-2-enamide (46.7 mg, 0.10 mmol) and 10% palladium carbon (10 mg, 0.09 mmol) in methanol (15 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 obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) and crystallized from ethyl acetate and hexane to give the title compound (26.2 mg, 0.054 mmol, 55.9%) as a white powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane)
  4. customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-6a5251b7472b442c8eced477dadcd104
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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