Water → 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl) methyl)sulfinyl)benzimidazol-6-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 856582노트

반응식

HRID 856582 반응식
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:33]=[CH:34][C:35]5[N:39]=[C:38]([S:40][CH2:41][C:42]6[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=6)[N:37]([CH3:50])[C:36]=5[CH:51]=4)=[O:30])=[CH:20][C:19]=3[CH:52]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:61])C=1.CSC.O>ClCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:33]=[CH:34][C:35]5[N:39]=[C:38]([S:40]([CH2:41][C:42]6[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=6)=[O:61])[N:37]([CH3:50])[C:36]=5[CH:51]=4)=[O:30])=[CH:20][C:19]=3[CH:52]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 695221267-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazol-6-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

생성물 1

HCID 695220727-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl) methyl)sulfinyl)benzimidazol-6-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide수율 3.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-13 °C

실험 절차

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazol-6-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (260 mg) in dichloromethane (10 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (133 mg) in dichloromethane (10 ml) at −78° C., and the mixture was stirred for 2.5 hours at −13° C. Dimethylsulfide (0.1 ml) was added to the mixture and the mixture was allowed to be at room temperature, and stirred for 30 minutes. To the mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was separated and purified by basic silica gel column chromatography (hexane:ethyl acetate=2:5→ethyl acetate), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[1-methyl-2-(((1-propylimidazol-5-yl) methyl)sulfinyl)benzimidazol-6-yl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (9 mg) (Compound 447) as yellow amorphous.

후처리

  1. customto be at room temperature
  2. stirringstirred for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was separated
  8. custompurified by basic silica gel column chromatography (hexane:ethyl acetate=2:5→ethyl acetate)

출처 및 근거

ORD 기록
ord-195e396becce4271ab3f8a77aac123df
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262185B2

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