Trifluoroacetic acid → HCID 44207663, compound

HRID 1677388Notes

Reaction equation

HRID 1677388 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH3:36])[C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[N:22]=2)[NH:17][CH:16]=1)=[O:14])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:36][C:9]1([C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=4)[N:22]=3)[NH:17][CH:16]=2)=[O:14])[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44207431HCID 44207431, compound

Product 1

HCID 44207663HCID 44207663, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (18 mg, 0.04 mmol) in anhydrous dichloromethane (3.0 ml) was added trifluoroacetic acid (1.0 ml, 13.5 mmol) dropwise. The reaction mixture was stirred for two days. The reaction mixture was partitioned between EtOAc/saturated aqueous Na2CO3. The organic layers were collected, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography using 0.5:9.5:90 concentrated aqueous NH4OH: MeOH: dichloromethane as eluant to provide 10 mg (70%) of (2-methyl-pyrrolidin-2-yl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a light yellow solid. M+H=397.

Workup

  1. customThe reaction mixture was partitioned between EtOAc/saturated aqueous Na2CO3
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-b77071e95a0f40e59879fbaad92b5306
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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