Methanol → HCID 57860750, compound

HRID 1947151Notes

Reaction equation

HRID 1947151 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][N:33]=4)[C:20](=[O:38])[C:19]=3[C:18]=2[O:39][CH3:40])=[O:16])[CH2:10][CH2:9]1)=[O:7])(=O)C.CO.[OH-].[Na+]>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]=[CH:34][N:33]=4)[C:20](=[O:38])[C:19]=3[C:18]=2[O:39][CH3:40])=[O:16])[CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66892732HCID 66892732, compound

Product 1

HCID 57860750HCID 57860750, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-[4-({[3-methoxy-1-methyl-4-oxo-5-(pyridin-2-ylmethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl]carbonyl}amino)piperidin-1-yl]-2-oxoethyl acetate (60 mg) in THF (2 mL)-methanol (2 ml) was added 2N sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 1 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. Recrystallization from ethyl acetate-diisopropyl ether gave the title compound (25 mg, 45%) as beige 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. customRecrystallization from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-8a5e5cd42da94834812d907a453f4a7d
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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