Methanol → HCID 57860636, compound

HRID 1947159Notes

Reaction equation

HRID 1947159 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:29]([CH3:30])[C:28]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:21]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[Cl:38])[C:20](=[O:39])[C:19]=3[C:18]=2[O:40][CH3:41])=[O:16])[CH2:10][CH2:9]1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C1COCC1.C(=O)([O-])O.[Na+]>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][N:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[N:29]([CH3:30])[C:17]([C:15]([NH:14][CH:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:13][CH2:12]3)=[O:16])=[C:18]([O:40][CH3:41])[C:19]=2[C:20]1=[O:39]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 66891712HCID 66891712, compound

Product 1

HCID 57860636HCID 57860636, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-[4-({[5-(2-chlorobenzyl)-3-methoxy-1-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl]carbonyl}amino)piperidin-1-yl]-2-oxoethyl acetate (80 mg) and potassium carbonate (100 mg, 0.71 mmol) in THF (2 mL)-methanol (1 mL)-water (1 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (8 mg, 2%) as white crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-63bd44de27794204a7a9e2a5406e3b8c
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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