Water → HCID 21360895, compound

HRID 1385112Notes

Reaction equation

HRID 1385112 reaction equation
C([O:8][NH:9][C:10]([CH2:12][NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH2:30][CH3:31])=[N:21][N:22]2[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15])=[O:11])C1C=CC=CC=1.O.C(OCC)(=O)C>CO.[Pd]>[OH:8][NH:9][C:10]([CH2:12][NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH2:30][CH3:31])=[N:21][N:22]2[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1)=[O:15])=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 21027785HCID 21027785, compound

Product 1

HCID 21360895HCID 21360895, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 120 mg (0.285 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid (benzyloxycarbamoyl-methyl)-amide and 0.08 g 10% Pd/C, 50% water wet, in 10 mL methanol and 10 mL ethyl acetate was placed on a Parr® hydrogenation apparatus and shaken under 30 psi H2 at room temperature for 40 minutes. The reaction mixture was filtered through Celite®, and the filtrate concentrated and dried to give 104 mg of a tan solid. Trituration with hexanes gave 69 mg (73%) of a tan crystalline powder: mp 105° C. (dec); HRMS calcd for C17H22N4O3+H: 331.1772. Found: 331.1769.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated
  3. customdried

Sources & evidence

ORD record
ord-d58e75f7405b431cb5b83150e8f95bb5
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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