HCID 67244859, compound → HCID 11995885, compound

HRID 733104Notes

Reaction equation

HRID 733104 reaction equation
C([N:8]1[N:12]=[N:11][C:10]([C:13]2([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27]([N:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]5([CH2:41][CH2:40][CH2:39][CH2:38]5)[C:30]4=[O:42])=[O:28])[CH2:21][CH2:20]3)[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[O:42]=[C:30]1[C:31]2([CH2:38][CH2:39][CH2:40][CH2:41]2)[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]1[C:27]([NH:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:13]2([C:10]3[N:9]=[N:8][NH:12][N:11]=3)[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:20][CH2:21]1)=[O:28]

Participants

4

Reactant 1

HCID 67244859HCID 67244859, compound

Product 1

HCID 11995885HCID 11995885, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[(1-{[1-(2-benzyl-2H-tetrazol-5-yl)cyclopentyl]methyl}piperidin-4-yl)methyl]-2′-oxospiro[cyclopentane-1,3′-indole]-1′(2′H)-carboxamide (120 mg, 0.21 mmol, step 6 of Example 14) and palladium hydroxide (20 mg, 20 wt. % palladium on carbon) in methanol (10 mL) was stirred for 8 h under H2 atmosphere. The mixture was filtered through a pad of Celite, and washed with methanol and the filtrate was concentrated to give a clear colorless oil. The residue was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (16:1) to give 80 mg (80%) of the title compound as a white solid. The solid was triturated with ethyl acetate/hexane and collected by filtration to give 72 mg (72%) of the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated
  4. customto give a clear colorless oil
  5. customThe residue was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (16:1)

Sources & evidence

ORD record
ord-51e77a59b8a94a33ae51d4da661b817a
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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