3-Pyridinecarboxaldehyde → HCID 67984922, compound

HRID 69005Notes

Reaction equation

HRID 69005 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]1=[O:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH2:27][N:26]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[N:10]([CH3:9])[C:11](=[O:34])[CH:12]=[CH:13]3)[CH:29]=1

Participants

6

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70656790HCID 70656790, compound

Product 1

HCID 67984922HCID 67984922, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Pyridine-3-carbaldehyde (0.076 ml) was added to a 1,2-dichloroethane solution (3 ml) of 1-methyl-6-{5-[(pyridin-3-ylmethyl)-amino]-pentyloxy}-1H-quinolin-2-one (237 mg). The mixture was stirred for 30 minutes at room temperature. Sodium triacetoxyborohydride (0.23 g) was added to the mixture, and the mixture was stirred at room temperature for 3 days. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1). The purified product was condensed under reduced pressure to give the title compound (247 mg) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-194ff3f2c243413bb364fc1d148bb880
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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