HCID 123283634, compound → HCID 71258404, compound

HRID 1506218Notes

Reaction equation

HRID 1506218 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]2[C:24]3[C:19](=[CH:20][N:21]=[C:22]4[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[CH:25][C:23]4=3)[C:18](=[O:36])[CH:17]=[CH:16]2)[CH2:9]1)C1C=CC=CC=1>CO.[C].[Pd]>[CH3:14][C@@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[N:15]1[C:24]2[C:19](=[CH:20][N:21]=[C:22]3[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[CH:25][C:23]3=2)[C:18](=[O:36])[CH:17]=[CH:16]1

Participants

4

Reactant 1

HCID 123283634HCID 123283634, compound

Product 1

HCID 71258404HCID 71258404, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

rac-1-[(3R,4R)-1-Benzyl-4-methylpiperidin-3-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (98 mg, 0.20 mmol) and 5% palladium-carbon (65 mg) in methanol (2 mL) were stirred at room temperature for 2 hours under a hydrogen atmosphere, then at 40° C. for 5 hours and at room temperature for one day. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a pale yellow amorphous (76.8 mg, yield 95%).

Workup

  1. waitat room temperature for one day
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-03e348e4c00c451a9d7d09a1130de0aa
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…