HCID 68516458, compound → HCID 68514451, compound

HRID 1717364Notes

Reaction equation

HRID 1717364 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][C:10]=1[N:20]1[C:24]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:23]([C:34]([NH:36][CH:37]2[CH2:39][CH2:38]2)=[O:35])[N:22]=[N:21]1)C1C=CC=CC=1>CO.[C].[Pd]>[CH2:27]([O:26][CH2:25][C:24]1[N:20]([C:10]2[CH:11]=[CH:12][C:13]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:9]=2[OH:8])[N:21]=[N:22][C:23]=1[C:34]([NH:36][CH:37]1[CH2:38][CH2:39]1)=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 68516458HCID 68516458, compound

Product 1

HCID 68514451HCID 68514451, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-{2-(Benzyloxy)-4-[(ethylamino)carbonyl]phenyl}-5-[(benzyloxy)methyl]-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide (205 mg, 0.390 mmol) obtained in Example 316 was dissolved in methanol (7.0 ml), and the mixture was stirred at room temperature for 4 hr in the presence of 10% palladium carbon (wet, purity 50%, 41 mg) under a hydrogen atmosphere. The reaction mixture was filtrated to remove the catalyst, and the filtrate was concentrated to dryness to give a colorless oil. This was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-4:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g), and the fraction obtained by elution with ethyl acetate-hexane (2:1-4:1) was concentrated and diluted with ethyl acetate-diethyl ether. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (131 mg, 0.301 mmol, 77.1%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give a colorless oil
  5. washThis was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-4:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g)
  6. customthe fraction obtained by elution with ethyl acetate-hexane (2:1-4:1)
  7. concentrationwas concentrated
  8. additiondiluted with ethyl acetate-diethyl ether
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-b23fc62a48f0436585774654afb304ea
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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