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

HRID 385674ノート

反応式

HRID 385674 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](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:23])[CH2:5][CH2:4]1.C[O-].[Na+].CO.[CH3:29][O:30][C:31]1[C:32]([CH3:39])=[CH:33][C:34]([CH:37]=O)=[N:35][CH:36]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O.C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[C:20]2[C:15]([CH:14]=[CH:13][C:12](=[O:23])[N:11]2[CH2:10][CH2:9][N:6]2[CH2:5][CH2:4][CH:3]([NH:2][CH2:37][C:34]3[CH:33]=[C:32]([CH3:39])[C:31]([O:30][CH3:29])=[CH:36][N:35]=3)[CH2:8][CH2:7]2)=[N:16][CH:17]=1

参加物

10

反応物 5

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23694274Sodium methanolate methanolHCID 578153485-Methoxy-4-methylpyridine-2-carbaldehydeHCID 689270711-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

生成物 1

HCID 578153787-methoxy-1-(2-(4-(((5-methoxy-4-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one収率 38.8%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

To a suspension of 0.20 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride in 2 mL of methanol, 0.28 g of a 28% sodium methoxide/methanol solution, 73 mg of 5-methoxy-4-methylpyridine-2-carbaldehyde and 28 μL of acetic acid were added. Then, 61 mg of sodium cyanoborohydride was added thereto, and the mixture was stirred at room temperature for 1 hour 30 minutes. To the reaction mixture, chloroform, a saturated aqueous sodium hydrogen carbonate solution and water were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was 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=93:7 to 86:14 to obtain 82 mg of 7-methoxy-1-(2-(4-(((5-methoxy-4-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one as a light yellow solid.

後処理

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

出典と根拠

ORDレコード
ord-a17909f325d94a829cdaf7947ea5cf6f
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

読み込み中…