Pyridine → HCID 58443370, 화합물

HRID 1969369노트

반응식

HRID 1969369 반응식
[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]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 2754Cilostazol2회HCID 783704-Chlorobutyryl chloride

생성물 1

HCID 58443370HCID 58443370, 화합물수율 42%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8d37c1dfceaf47b99324704f38ef32b8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426597B2

반응 노트

불러오는 중…