HCID 57664895, compound → HCID 57665212, compound

HRID 1717361Notes

Reaction equation

HRID 1717361 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][CH2:26][CH3:27])=[C:23]([C:28]([NH:30][CH:31]2[CH2:33][CH2:32]2)=[O:29])[N:22]=[N:21]1)C1C=CC=CC=1>CO.[C].[Pd]>[CH:31]1([NH:30][C:28]([C:23]2[N:22]=[N:21][N:20]([C:10]3[CH:11]=[CH:12][C:13]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:9]=3[OH:8])[C:24]=2[CH2:25][CH2:26][CH3:27])=[O:29])[CH2:33][CH2:32]1

Participants

4

Reactant 1

HCID 57664895HCID 57664895, compound

Product 1

HCID 57665212HCID 57665212, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-{2-(Benzyloxy)-4-[(ethylamino)carbonyl]phenyl}-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide compound (582 mg, 1.30 mmol) obtained in Example 312 was dissolved in methanol (20 ml), and the mixture was stirred at room temperature for 4 hr in the presence of 10% palladium carbon (wet, purity 50%, 116 mg) under a hydrogen atmosphere. The reaction mixture was filtrated to removed the catalyst, and the filtrate was concentrated to dryness to give a yellow oil. This was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:2-7:3) on silica gel (manufactured by E. Merck, Art.7734, 10 g), and the object fraction 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 (409 mg, 1.14 mmol, 88.0%).

Workup

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

Sources & evidence

ORD record
ord-4c8a028fa1184041aacc1038c8a7630c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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