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

HRID 39814

반응식

HRID 39814 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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 μL 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.

후처리

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

출처 및 근거

ORD 기록
ord-a3e767bd9a5347eb9c1a95225a49d6e7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524738B2

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