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

HRID 77786

反応式

HRID 77786 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-791513e75ff44e2d89be8018f7f5923e
出典データセット
uspto-grants-2014_09
特許番号
US08841336B2

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