Sodium Chloride → 6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzoxazin-3(4H)-one hydrochloride

HRID 385632Notes

Reaction equation

HRID 385632 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:12][C:11]2=[O:20])[CH2:4][CH2:3]1.[O:21]=[C:22]1[NH:27][C:26]2[CH:28]=[C:29]([CH:32]=O)[CH:30]=[CH:31][C:25]=2[O:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl-:53].[Na+]>ClCCl.C(Cl)(Cl)Cl.O.C(O)(=O)C>[ClH:53].[O:20]=[C:11]1[CH:12]=[CH:13][C:14]2[C:19](=[N:18][CH:17]=[CH:16][CH:15]=2)[N:10]1[CH2:9][CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:32][C:29]2[CH:30]=[CH:31][C:25]3[O:24][CH2:23][C:22](=[O:21])[NH:27][C:26]=3[CH:28]=2)[CH2:3][CH2:4]1

Participants

10

Reactant 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehydeHCID 578152591-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689284286-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzoxazin-3(4H)-one hydrochloride

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 83 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one in 15 mL of dichloromethane, 54 mg of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde, 86 μL of acetic acid and 0.36 g of sodium triacetoxyborohydride were dividedly added while reacting at room temperature for 1.5 days. To the reaction solution, water, a saturated aqueous sodium hydrogen carbonate solution, chloroform and sodium chloride were added, the organic layer was separated, and the aqueous layer was extracted with chloroform while salting out. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=5:1, and the resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid, and then, the solvent was distilled off under reduced pressure. Diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 0.12 g of 6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-1,4-benzoxazin-3(4H)-one hydrochloride as a light yellow solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography
  6. dissolutionmethanol=5:1, and the resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionDiethyl ether was added to the resultant residue
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-12c86f918f294dcd80fcbc9f2fc97d26
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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