HCID 178433754, compound → HCID 178433752, compound

HRID 2282202Notes

Reaction equation

HRID 2282202 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([CH3:34])[C:17]([C:18]3[S:19][C:20]([C:29]4[NH:33][CH:32]=[N:31][N:30]=4)=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:22]=3)=[C:11]2[CH:10]=1)C1C=CC=CC=1>O1CCCC1.CO.C(O)C.[C].[Pd]>[CH3:34][C:16]1[C:17]([C:18]2[S:19][C:20]([C:29]3[NH:33][CH:32]=[N:31][N:30]=3)=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:22]=2)=[C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][N:12]2[N:15]=1

Participants

6

Reactant 1

HCID 178433754HCID 178433754, compound

Product 1

HCID 178433752HCID 178433752, compoundYield 38.6%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(benzyloxy)-2-methyl-3-[4-phenyl-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridine (220 mg, 0.47 mmol) produced in Example 30(x) in tetrahydrofuran (20 mL) and methanol (10 mL) was added 10% palladium-carbon (50% wet with water, 110 mg). Under a hydrogen atmosphere (1 atm), the mixture was stirred at room temperature for 31 hr, and 10% palladium-carbon was filtered off. The filtrate was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0), and the obtained solution was concentrated under reduced pressure. The obtained residue was washed with tetrahydrofuran/ethyl acetate. The obtained crude product was dissolved in ethanol, and concentrated under reduced pressure. The obtained residue was crystallized from ethanol and ethyl acetate to give the title compound (68 mg, 38%) as a pale yellow-brown solid.

Workup

  1. filtration10% palladium-carbon was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)
  4. concentrationthe obtained solution was concentrated under reduced pressure
  5. washThe obtained residue was washed with tetrahydrofuran/ethyl acetate
  6. customThe obtained crude product
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was crystallized from ethanol and ethyl acetate

Sources & evidence

ORD record
ord-56cfb7204f234564b06f7df04d0a98e8
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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