Sodium Bicarbonate → HCID 57815245, compound

HRID 385677Notes

Reaction equation

HRID 385677 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:23])[CH2:5][CH2:4]1.C[O-].[Na+].CO.[CH2:29]([C:31]1[C:38]([F:39])=[CH:37][C:34]([CH:35]=O)=[CH:33][N:32]=1)[CH3:30].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl.C(O)(=O)C>[CH2:29]([C:31]1[N:32]=[CH:33][C:34]([CH2:35][NH:2][CH:3]2[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][N:11]3[C:20]4[C:15](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[CH:14]=[CH:13][C:12]3=[O:23])[CH2:7][CH2:8]2)=[CH:37][C:38]=1[F:39])[CH3:30]

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 23694274Sodium methanolate methanolHCID 57815447HCID 57815447, compoundHCID 689270711-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

Product 1

HCID 57815245HCID 57815245, compoundYield 34.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 0.14 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride in 2 mL of methanol, 0.20 g of a 28% sodium methoxide/methanol solution, 53 mg of 6-ethyl-5-fluoronicotinaldehyde and 20 μL of acetic acid were added. Then, 43 mg of sodium cyanoborohydride was added thereto, and the mixture was stirred at room temperature for 1 hour 20 minutes. Thereto was further added 43 mg of sodium cyanoborohydride, and the mixture was stirred at room temperature for 1 hour, and then stirred at 30 to 40° C. for 1 hour. To the reaction mixture, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using gradient elution with chloroform:methanol=93:7 to 9:1 to obtain 53 mg of 1-(2-(4-(((6-ethyl-5-fluoropyridin-3-yl)methyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one as a light yellow oily substance.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. stirringstirred at 30 to 40° C. for 1 hour
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. washthe resultant solution was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by basic silica gel column chromatography
  10. washelution with chloroform

Sources & evidence

ORD record
ord-f85973213a4a4c2dbd229598d99cf029
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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