Methanol → HCID 57860019, compound

HRID 1947153Notes

Reaction equation

HRID 1947153 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]=[C:34]([O:38][C:39]([F:42])([F:41])[F:40])[CH:33]=4)[C:20](=[O:43])[C:19]=3[C:18]=2[O:44][CH3:45])=[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+]>[OH: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]=[C:34]([O:38][C:39]([F:41])([F:42])[F:40])[CH:33]=4)[C:20](=[O:43])[C:19]=3[C:18]=2[O:44][CH3:45])=[O:16])[CH2:10][CH2:9]1)=[O:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 66892980HCID 66892980, compound

Product 1

HCID 57860019HCID 57860019, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-{4-[({3-methoxy-1-methyl-4-oxo-5-[3-(trifluoromethoxy)benzyl]-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl}carbonyl)amino]piperidin-1-yl}-2-oxoethyl acetate (70 mg) and potassium carbonate (77 mg, 0.55 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 (23 mg, 4%) 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-297c747ca5c948a8b332b57fe2e5026a
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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