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Sodium hydride → 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 1586835
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HRID 1586835 반응식
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]2[C:10]([N:16]=1)=[N:11][CH:12]=[CH:13][C:14]=2[CH3:15])[CH2:4][CH2:5][CH3:6].[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[C:24]([C:39]2[N:43]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:42]=[N:41][N:40]=2)[N:25]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33]OS(C)(=O)=O)=[CH:29][CH:28]=2)[CH:26]=1)=[O:21])[CH3:18]>CS(C)=O.[Cl-].[Na+].O>[CH2:3]([C:7]1[N:16]([CH2:33][C:30]2[CH:29]=[CH:28][C:27]([N:25]3[CH:26]=[C:22]([C:20]([O:19][CH2:17][CH3:18])=[O:21])[CH:23]=[C:24]3[C:39]3[N:43]([C:44]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:42]=[N:41][N:40]=3)=[CH:32][CH:31]=2)[C:10]2=[N:11][CH:12]=[CH:13][C:14]([CH3:15])=[C:9]2[N:8]=1)[CH2:4][CH2:5][CH3:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 150152652-Butyl-7-methyl-1H-imidazo[4,5-b]pyridineHCID 197593244-ethoxycarbonyl-1-(4-methanesulfonyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole

생성물 1

HCID 197592572-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine수율 66.7%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
2회
HCID 57417360Sodium chloride; water용매

실험 절차

Sodium hydride (10 mg) (60% in oil) was added to a stirred solution of 2-butyl-7-methylimidazo[4,5-b]pyridine (48 mg) in dimethyl sulfoxide (5.0 ml) and the mixture was stirred for 30 minutes at ambient temperature. To this mixture was added a solution of 4-ethoxycarbonyl-1-(4-methanesulfonyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole (193 mg) in dimethyl sulfoxide (2 ml). The mixture was stirred for 3 hours at ambient temperature and poured into brine. The mixture was extracted with ethyl acetate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography to afford 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (123 mg) as a colorless viscous oil.

후처리

  1. stirringThe mixture was stirred for 3 hours at ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-a773045f6ed74fae9ddda5f8254808df
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05215994

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