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

HRID 2193187ノート

反応式

HRID 2193187 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-ff035dca3fd7494581a8bc7e1024c838
出典データセット
uspto-grants-2012_12
特許番号
US08329694B2

反応ノート

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