HCID 15547425, compound → HCID 15547426, compound

HRID 1385105Notes

Reaction equation

HRID 1385105 reaction equation
C([O:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[CH:29]=[C:28]3[C:24]([C:25]([CH2:35][CH3:36])=[N:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[O:20])=[CH:14][CH:13]=1)=[O:11])C1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[OH:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[CH:29]=[C:28]3[C:24]([C:25]([CH2:35][CH3:36])=[N:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[O:20])=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 1

HCID 15547425HCID 15547425, compound

Product 1

HCID 15547426HCID 15547426, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 187 mg (0.387 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid (4-benzyloxycarbamoyl-phenyl)-amide and 200 mg 10% Pd/C in 10 mL ethyl acetate and 10 mL methanol was placed on a Parr® hydrogenation appartus and shaken under 30 psi H2 at room temperature for 1 hour. The reaction mixture was filtered through Celite®, and the filtrate concentrated and dried to give a tan solid. Purification on a silica gel column (CH3OH/CH2Cl2 gradient 4%, 10%, 20%, flash) gave 74 mg (49%) of a tan solid: mp 175° C. (dec); HRMS calcd for C22H24N4O3+H: 393.1928. Found: 393.1949.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated
  3. customdried
  4. customto give a tan solid
  5. customPurification on a silica gel column (CH3OH/CH2Cl2 gradient 4%, 10%, 20%, flash)

Sources & evidence

ORD record
ord-12812241efe84a71af79837b70e06d0c
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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