Sodium Bicarbonate → 1-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

HRID 2193187Notes

Reaction equation

HRID 2193187 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](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([NH:23][CH3:24])=[O:22])=[CH:13][C:12]2=[O:25])[CH2:5][CH2:4]1.C([BH3-])#N.[Na+].[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[CH3:39])[CH:34]=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.CO>[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[CH3:39])[CH2:34][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([NH:23][CH3:24])=[O:22])=[CH:13][C:12]2=[O:25])[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27745743-Fluoro-4-methylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 675390731-(2-(4-aminopiperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride

Product 1

HCID 593984361-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To 3.0 mL of methanol suspension containing 0.12 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride, 38 mg of sodium cyanoborohydride, 37 W., of 3-fluoro-4-methylbenzaldehyde and 69 μL of acetic acid were added at room temperature and stirred at the same temperature for 3 hours. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added to be adjusted to pH 10, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30], to give 26 mg of 1-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide as a white solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. washwashed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30]

Sources & evidence

ORD record
ord-ff035dca3fd7494581a8bc7e1024c838
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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