HCID 68517686, compound → HCID 68518208, compound

HRID 1717378Notes

Reaction equation

HRID 1717378 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][CH2:27][O:28]CC2C=CC=CC=2)=[C:23]([C:36]([NH:38][CH:39]2[CH2:41][CH2:40]2)=[O:37])[N:22]=[N:21]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH:39]1([NH:38][C:36]([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][CH2:27][OH:28])=[O:37])[CH2:41][CH2:40]1

Participants

4

Reactant 1

HCID 68517686HCID 68517686, compound

Product 1

HCID 68518208HCID 68518208, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-{2-(benzyloxy)-4-[(ethylamino)carbonyl]phenyl}-5-[3-(benzyloxy)propyl]-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide (1.17 g) obtained in Example 335b) in ethanol (50 ml) was added 10% Pd(OH)2/C (120 mg), and the mixture was stirred under 5 atm at 80° C. for 2 hr. The reaction mixture was filtered through celite, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=5/1) to give the title compound as a white powder (520 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=5/1)

Sources & evidence

ORD record
ord-6a7b6b6c278649df976f3402688f7465
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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