6-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one → 6-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

HRID 12280

반응식

HRID 12280 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]3[CH:30]=[C:31]([C:34](OC)=[O:35])[CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1>ClCCl.C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2].[O-2].[Mn+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[C:20]3[CH:30]=[C:31]([CH:34]=[O:35])[CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1

참가 물질

6

반응물 1

HCID 686813496-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

생성물 1

HCID 866116086-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

시약·촉매·용매 4

HCID 160959Manganese oxide촉매HCID 178418406HCID 178418406, 화합물촉매HCID 1140Toluene용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

6-Chloro-4-(6-methoxycarbonyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (3.0 g, 5.3 mmol) is dissolved in dichloromethane, and the solution is cooled to 0° C. 15% DIBA1H in toluene is added dropwise, and the reaction mixture is stirred at room temperature for 1 hour. A further 15% DIBA1H in toluene is then added dropwise at 0° C. and stirred at room temperature for 1 hour. Manganese(IV) oxide is then added directly and the reaction solution is heated to reflux for 3 hours. Additional manganese oxide is added every 3 hours until the conversion is complete according to LC-MS. The reaction solution is filtered through kieselguhr, the residue is washed several times with dichloromethane, and the solvent is removed in a rotary evaporator.

후처리

  1. stirringstirred at room temperature for 1 hour
  2. temperaturethe reaction solution is heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe reaction solution is filtered through kieselguhr
  5. washthe residue is washed several times with dichloromethane
  6. customthe solvent is removed in a rotary evaporator

출처 및 근거

ORD 기록
ord-2bb6dd6c1f964b519f78e8c155863158
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727989B2

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