HCID 57664965, compound → HCID 57664851, compound

HRID 1717318Notes

Reaction equation

HRID 1717318 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)[N:14]=[N:13][C:12]=1[C:27]([NH:29][CH:30]1[CH2:32][CH2:31]1)=[O:28])C1C=CC=CC=1>CO.C(O)(=O)C.[C].[Pd]>[CH:30]1([NH:29][C:27]([C:12]2[N:13]=[N:14][N:15]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=3)[C:11]=2[CH2:10][CH2:9][OH:8])=[O:28])[CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 57664965HCID 57664965, compound

Product 1

HCID 57664851HCID 57664851, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

5-[2-(Benzyloxy)ethyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (737 mg, 1.70 mmol) obtained in Example 107 was dissolved in methanol-acetic acid (25:1, 26 ml), and the mixture was stirred at room temperature for 63 hr in the presence of 10% palladium carbon (wet, purity 50%, 150 mg) under a hydrogen atmosphere. The reaction mixture was filtered to remove the catalyst, the filtrate was concentrated to dryness, and ethyl acetate-diethyl ether was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (480 mg, 1.40 mmol, 82.2%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to dryness, and ethyl acetate-diethyl ether
  4. additionwas added
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-8fc1aeab47244c4481b79167cf94cff2
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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