Sodium Hydroxide → HCID 59540549, compound

HRID 1677493Notes

Reaction equation

HRID 1677493 reaction equation
[CH3:1][C:2]1([C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[N:20]=3)[NH:15][CH:14]=2)=[O:12])[CH2:7][CH2:6][CH:5]([O:8]C=O)[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[OH:8][CH:5]1[CH2:4][CH2:3][C:2]([C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=4)[N:20]=3)[NH:15][CH:14]=2)=[O:12])([CH3:1])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59540634HCID 59540634, compound

Product 1

HCID 59540549HCID 59540549, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of formic acid 4-methyl-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-cyclohexyl ester (12 mg, 0.026 mmol) in MeOH (1 ml) was treated with 2N NaOH aq. (0.2 ml, 0.4 mmol) and allowed to stir at 50° C. for overnight. The reaction mixture was partitioned between EtOAc/sat. NH4Cl aq., and the organic layers were collected and concentrated. Silica gel chromatography using 0-10% {5% NH4OH:MeOH} in DCM as eluant gave 10 mg (89%) of (4-hydroxy-1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a white solid. M+H=426.

Workup

  1. customThe reaction mixture was partitioned between EtOAc/
  2. customNH4Cl aq., and the organic layers were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9125424beea64f13981a22259bfdba84
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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