Sodium Bicarbonate → 7-methoxy-1-(2-(4-(((4-methoxy-5-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one

HRID 385672ノート

反応式

HRID 385672 の反応式
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH:10]=O)[CH:4]=1.C[O-].[Na+].CO.Cl.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]2[C:36]3[C:31](=[N:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=3)[CH:30]=[CH:29][C:28]2=[O:39])[CH2:21][CH2:20]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:38][O:37][C:34]1[CH:35]=[C:36]2[C:31]([CH:30]=[CH:29][C:28](=[O:39])[N:27]2[CH2:26][CH2:25][N:22]2[CH2:21][CH2:20][CH:19]([NH:18][CH2:10][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=3)[CH2:24][CH2:23]2)=[N:32][CH:33]=1

参加物

9

反応物 5

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23694274Sodium methanolate methanolHCID 578154004-Methoxy-5-methylpyridine-2-carbaldehydeHCID 689270711-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

生成物 1

HCID 578151937-methoxy-1-(2-(4-(((4-methoxy-5-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one収率 63.3%

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 a solution of 71 mg of 4-methoxy-5-methylpyridine-2-carbaldehyde in 2 mL of methanol, 0.27 g of a 28% sodium methoxide/methanol solution, 0.19 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride and 27 μL of acetic acid were added. Then, 59 mg of sodium cyanoborohydride was added thereto and the mixture was stirred at room temperature for 4 hours. To the reaction mixture, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added. The organic layer was separated, 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=19:1 to 86:14 to obtain 0.13 g of 7-methoxy-1-(2-(4-(((4-methoxy-5-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one as a yellow oily substance.

後処理

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by basic silica gel column chromatography
  6. washelution with chloroform

出典と根拠

ORDレコード
ord-0d7c1424627041f9bfb695443b0cd96f
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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