Silicon tetrachloride → 3-(5-Chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl ester

HRID 77786

반응식

HRID 77786 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)[CH:5]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Si](Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[N:26][N:25]=[N:24]2)[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)[CH:5]=1

참가 물질

6

반응물 4

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 578514303-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester

생성물 1

HCID 578516043-(5-Chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl ester수율 90.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

3-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester (1.90 g, 5.71 mmol) was dissolved in acetonitrile, and NaN3 (3.71 g, 5.71 mmol) and SiCl4 (1.64 mL, 14.28 mmol) were added. The reaction mixture was stirred at 60° C. for 18 hours, then cooled and poured in to cold saturated aqueous NaHCO3. The resulting mixture was extracted with EtOAc, and the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to give 1.84 g of 3-(5-chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl ester, MS (M+H)=358.

후처리

  1. temperaturecooled
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-791513e75ff44e2d89be8018f7f5923e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841336B2

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