Sodium Bicarbonate → HCID 57860018, compound

HRID 1513581Notes

Reaction equation

HRID 1513581 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]([C:12]1[N:24]([CH3:25])[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]([CH2:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:15](=[O:35])[C:14]=2[C:13]=1[O:36][CH3:37])=[O:11].C(=O)([O-])O.[Na+]>>[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]([C:12]1[N:24]([CH3:25])[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]([CH2:26][C:27](=[O:34])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:15](=[O:35])[C:14]=2[C:13]=1[O:36][CH3:37])=[O:11]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 66893033HCID 66893033, compound

Product 1

HCID 57860018HCID 57860018, compoundYield 33%

Procedure

To the thus-obtained N-[trans-2-aminocyclohexyl]-3-methoxy-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]quinoline-2-carboxamide hydrochloride was added saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=20/1), and the obtained solid was recrystallized from ethyl acetate-ethanol to give the title compound (80.0 mg, 33%) as white crystals.

Workup

  1. extractionthe mixture was extracted 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 purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=20/1)
  6. customthe obtained solid was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-aab2472c279449a7874cccd43ac7adea
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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