Pyridine → HCID 58443370、化合物

HRID 1969369ノート

反応式

HRID 1969369 の反応式
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:34][CH2:35][CH2:36][CH2:37][C:38](Cl)=[O:39]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:34][CH2:35][CH2:36][CH2:37][C:38]([N:23]1[C:24]2[C:19](=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]3[N:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[N:8]=[N:9][N:10]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:21][C:22]1=[O:27])=[O:39]

参加物

6

反応物 3

HCID 1049PyridineHCID 2754Cilostazol2 回HCID 783704-Chlorobutyryl chloride

生成物 1

HCID 58443370HCID 58443370、化合物収率 42%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one (cilostazol, 1, A=H, 15.00 g, 40.6 mmol), pyridine (6.42 g, 81.2 mmol) and 4-dimethyl-aminopyridine (DMAP, 6.45 g, 52.8 mmol) in 135 mL chloroform at room temperature is added slowly 4-chlorobutanoyl chloride (7.45 g, 52.8 mmol). The mixture is stirred at 70° C. for 20 hours. The reaction mixture is diluted with 1000 mL CH2Cl2, and washed with 1N HCl, saturated NaHCO3 solution and brine. The organic phase is dried over sodium sulphate, and concentrated. The residue is purified by flash chromatography (silica gel, CH2Cl2/tert-butyl methyl ether 90:10) to give the title compound in 42% yield.

後処理

  1. washwashed with 1N HCl, saturated NaHCO3 solution and brine
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography (silica gel, CH2Cl2/tert-butyl methyl ether 90:10)

出典と根拠

ORDレコード
ord-8d37c1dfceaf47b99324704f38ef32b8
出典データセット
uspto-grants-2013_04
特許番号
US08426597B2

反応ノート

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