HCID 59540703, compound → HCID 59540549, compound

HRID 1677491Notes

Reaction equation

HRID 1677491 reaction equation
C([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[C:24]([C:27]4[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=4)[N:25]=3)[NH:20][CH:19]=2)=[O:17])([CH3:15])[CH2:11][CH2:10]1)C1C=CC=CC=1>C1COCC1.CCO.[Pd]>[OH:8][CH:9]1[CH2:10][CH2:11][C:12]([C:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[C:24]([C:27]4[CH:28]=[C:29]([O:37][CH3:38])[C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=4)[N:25]=3)[NH:20][CH:19]=2)=[O:17])([CH3:15])[CH2:13][CH2:14]1

Participants

5

Reactant 1

HCID 59540703HCID 59540703, compound

Product 1

HCID 59540549HCID 59540549, compoundYield 130.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-benzyloxy-1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (36 mg, 0.070 mmol) and 10% Pd/C (10 mg), in THF (10 ml) and EtOH (8 ml), was hydrogenated for 5 days under a 60 psi H2 atmosphere. The reaction mixture was vacuum purged with argon (3×), and filtered through a plug of celite using THF and DCM. The filtrate was concentrated giving an opaque oil which was purified by silica gel chromatography using 0-10% MeOH in EtOAc as eluant provided 39 mg (36%) of (4-hydroxy-1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a pale yellow solid. MP 242-244° C. M+H=426.

Workup

  1. custompurged with argon (3×)
  2. filtrationfiltered through a plug of celite
  3. concentrationThe filtrate was concentrated
  4. customgiving an opaque oil which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-1bf69af1cae44e3e8f010323eac26c09
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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