Methanol → HCID 10194752, compound

HRID 750152Notes

Reaction equation

HRID 750152 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:30][C:31]2[CH:39]=[CH:38][C:34]3[O:35][CH2:36][O:37][C:33]=3[CH:32]=2)[C:7](=[O:29])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([NH:21]CC1C=CC=CC=1)=[CH:10][CH:9]=2)=[O:4].CO.[H][H]>[C].[Pd].C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:30][C:31]2[CH:39]=[CH:38][C:34]3[O:35][CH2:36][O:37][C:33]=3[CH:32]=2)[C:7](=[O:29])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([NH2:21])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 69156557HCID 69156557, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10194752HCID 10194752, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-benzylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (670 mg), 10% palladium carbon (200 mg), methanol (10 ml) and THF (10 ml) was stirred at room temperature at 4-5 atm hydrogen pressure for 48 hrs. Palladium carbon was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized (ethyl acetate-hexane) to give the title compound (400 mg).

Workup

  1. filtrationPalladium carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  4. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-afd71ddd0cb047478987b6584fe942d7
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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