HCID 68516458, compound → HCID 57665023, compound

HRID 1717363Notes

Reaction equation

HRID 1717363 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]CC2C=CC=CC=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(O)(=O)C.[C].[Pd]>[CH:37]1([NH:36][C:34]([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][OH:26])=[O:35])[CH2:39][CH2:38]1

Participants

4

Reactant 1

HCID 68516458HCID 68516458, compound

Product 1

HCID 57665023HCID 57665023, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

1-{2-(Benzyloxy)-4-[(ethylamino)carbonyl]phenyl}-5-[(benzyloxy)methyl]-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide (1.50 g, 2.85 mmol) obtained in Example 316 was dissolved in methanol-acetic acid (9:1, 50 ml), and the mixture was stirred at room temperature for 68 hr in the presence of 10% palladium carbon (wet, purity 50%, 300 mg) under a hydrogen atmosphere. The reaction mixture was filtrated to remove the catalyst, the filtrate was concentrated, diluted with toluene (100 ml) and concentrated, and ethyl acetate was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (1.00 g, quant.). This powder (0.700 g) was crystallized from ethyl acetate, washed with ethyl acetate and diethyl ether and dried to give the title compound as a white powder (637 mg, 1.84 mmol, 64.7%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. additiondiluted with toluene (100 ml)
  5. concentrationconcentrated
  6. additionethyl acetate was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-20a3aec6c16f41fd81cf860540fe4778
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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