Potassium Hydroxide → HCID 44199846, compound

HRID 1642086Notes

Reaction equation

HRID 1642086 reaction equation
[CH2:1]([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](Br)[N:25]=3)[NH:20][CH:19]=2)=[O:17])([CH3:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CCO.[Pd]>[CH2:1]([O:8][CH:9]1[CH2:10][CH2:11][C:12]([C:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][N:25]=3)[NH:20][CH:19]=2)=[O:17])([CH3:15])[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 44199845HCID 44199845, compound

Product 1

HCID 44199846HCID 44199846, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (4-benzyloxy-1-methyl-cyclohexyl)-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanone (13 mg, 0.03 mmol), KOH (1 mg, 0.02 mmol), and 10% Pd/C (10 mg), in EtOH (8 ml), was hydrogenated for 2 days under H2 atmosphere (1 atm). The reaction mixture was filtered through a plug of celite using THF and DCM. The filtrate was concentrated to a white solid, which was purified by silica gel chromatography using 0-70% Et2O in DCM as eluant providing 9 mg (82%) of (4-benzyloxy-1-methyl-cyclohexyl)-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanone as a white solid. M+H=350.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. concentrationThe filtrate was concentrated to a white solid, which
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-962cf07b2da24c91bf2cddbf87cfbf2f
Source dataset
uspto-grants-2012_02
Patent number
US08119636B2

Reaction notes

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