Ammonium Hydroxide → HCID 9936150, compound

HRID 1532360Notes

Reaction equation

HRID 1532360 reaction equation
C(OC(=O)[N:10]([CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[O:33])[CH:30]=2)[NH:25][C:24]=1[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H].[NH4+].[OH-]>[OH-].[OH-].[Pd+2].COCCO>[CH3:47][C:42]1[CH:41]=[C:40]([C:24]2[NH:25][C:26]3[C:31]([C:23]=2[CH2:22][CH2:21][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:30][C:29]([C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:33])=[CH:28][CH:27]=3)[CH:45]=[C:44]([CH3:46])[CH:43]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 53851224HCID 53851224, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9936150HCID 9936150, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 113 mg (0.175 mmol) of [2-[2-(3,5-dimethylphenyl)-5-(morpholine-4-carbonyl)-1H-indol-3-yl]ethyl]-(4-pyridin-4-ylbutyl)carbamic acid benzyl ester, 50 mg of 20% palladium hydroxide on carbon, and 10 mL of 2-methoxyethanol was shaken with hydrogen (approx. 50 psig) in a pressure vessel for 2.5 hours. The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (gradient elution from 99:1:0.1 to 94:6:0.6 CH2Cl2-MeOH-concd. NH4OH) yielded 53.2 mg (60%) of a white, stiff foam; homogeneous by TLC in 95:5:0.5 CH2Cl2-MeOH-concd. NH4OH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e=511.5 (M+H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (gradient elution from 99:1:0.1 to 94:6:0.6 CH2Cl2-MeOH-concd. NH4OH)
  4. customyielded 53.2 mg (60%) of a white, stiff foam

Sources & evidence

ORD record
ord-59b6a238cba145abba76615aea535281
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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