Stannous chloride dihydrate → Methyl 2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

HRID 1181333노트

반응식

HRID 1181333 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][C:9]=2[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[C:21]4[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:20]=4[N:19]=3)=[C:14]([F:37])[CH:13]=2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:42][C:39]1[CH:40]=[CH:41][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([CH:38]=1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:21]3[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:20]=3[N:19]=2)=[C:14]([F:37])[CH:13]=1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 21943015HCID 21943015, 화합물

생성물 1

HCID 21943052Methyl 2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate수율 83%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Methyl 2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate (1.9 g) obtained in Example 337 was suspended in ethanol (40 ml), and tin(II) chloride dihydrate (3.5 g) was added, which was followed by refluxing under heating for 30 min. The reaction mixture was concentrated under reduced pressure, 4N sodium hydroxide was added and the mixture was extracted with chloroform. The organic layer was washed with 2N sodium hydroxide and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diisopropyl ether was added to the residue, and the precipitated crystals were collected by filtration to give the title compound (1.5 g, yield 82%).

후처리

  1. temperatureby refluxing
  2. temperatureunder heating for 30 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure, 4N sodium hydroxide
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with 2N sodium hydroxide and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionDiisopropyl ether was added to the residue
  10. filtrationthe precipitated crystals were collected by filtration

출처 및 근거

ORD 기록
ord-11699579c2ef4e74a3642a6b2ed805b4
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285551B2

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