Acetic Anhydride → HCID 59540833, compound

HRID 1677389Notes

Reaction equation

HRID 1677389 reaction equation
[CH3:1][C:2]1([C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][NH:3]1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl>[CH3:1][C:2]1([C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][N:3]1[C:30](=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 44207663HCID 44207663, compound

Product 1

HCID 59540833HCID 59540833, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-methyl-pyrrolidin-2-yl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (8 mg, 0.02 mmol) in anhydrous dichloromethane (0.3 ml) was cooled to 0° C. and treated with acetic anhydride (2 mg, 0.02 mmol). The reaction mixture was stirred for 1 hour and then allowed to warm to room temperature and stir for 3 hours. The reaction mixture was partitioned between EtOAc/saturated aqueous NaHCO3. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a brownish oil. The residue was purified by preparative thin layer chromatography using 50% EtOAc in hexanes as eluant to provide 2 mg (17%) of 1-{2-methyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-pyrrolidin-1-yl}-ethanone as a light yellow solid. M+H=439.

Workup

  1. stirringstir for 3 hours
  2. customThe reaction mixture was partitioned between EtOAc/saturated aqueous NaHCO3
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving a brownish oil
  8. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-9c957d4fbb924e4392d17dea23070f6f
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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