Chloroform methanol → 1-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

HRID 1506241Notes

Reaction equation

HRID 1506241 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=[CH:24][C:22]4=3)[C:17](=[O:35])[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(Cl)(Cl)Cl.CO>CO.[C].[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH:25]=[CH:24][C:22]4=3)[C:17](=[O:35])[CH:16]=[CH:15]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 21584188Chloroform methanolHCID 712584011-(1-Benzylpiperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one

Product 1

HCID 712582261-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-oneYield 68%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-(1-Benzylpiperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (341 mg, 0.697 mmol) in methanol was stirred with 5% palladium-carbon (500 mg) for one day under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hi Flash column amino type manufactured by Yamazen Corporation: chloroform/methanol=9/1/(v/v)) to give the title compound (189 mg, yield 68%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (Hi Flash column amino type

Sources & evidence

ORD record
ord-c4cbe7a83e944ed7a71c2714694b47f5
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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