Hydrochloric Acid → 6-{3-[N-(3-hydroxymethylbenzyl)-N-(2-pyridin-3-ylethyl)amino]prop oxy}-1-methyl-1H-quinolin-2-one dihydrochloride

HRID 69020Notes

Reaction equation

HRID 69020 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[N:32]([CH3:36])[C:31](=[O:37])[CH:30]=[CH:29]3)[CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=1.CO.[ClH:41]>C(OCC)(=O)C.O>[ClH:41].[ClH:41].[OH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][N:13]([CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[C:31](=[O:37])[CH:30]=[CH:29]2)[CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 90229760HCID 90229760, compound

Product 1

HCID 669611786-{3-[N-(3-hydroxymethylbenzyl)-N-(2-pyridin-3-ylethyl)amino]prop oxy}-1-methyl-1H-quinolin-2-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Sodium borohydride (16.5 mg) was added to a THE solution (4 ml) of 3-{[N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(2-pyridin-3-ylethyl)amino]methyl}benzoic acid methyl ester (192 mg). Methanol (1 ml) was added to the mixture and stirred for 1.5 hour while heated under reflux. The reaction liquid was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride in ethyl acetate solution (0.082 ml) was added to a ethyl acetate solution (1 ml) of the residue, and the liquid was stirred at room temperature. The precipitated insoluble matter was separated, washed with ether, and dried to give the title compound (53.4 mg) as a white powder.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. extractionfollowed by extraction with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1)
  8. customcondensed under reduced pressure
  9. stirringthe liquid was stirred at room temperature
  10. customThe precipitated insoluble matter was separated
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-2d51b09151a6466187dc37ef70f780ba
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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