Dimethyl Sulfoxide → 2-Piperazin-1-yl-6-trifluoromethyl-1H-benzoimidazole

HRID 730703ノート

反応式

HRID 730703 の反応式
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=2[N:3]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CS(C)=O>O>[N:15]1([C:2]2[NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazole

生成物 1

HCID 116662012-Piperazin-1-yl-6-trifluoromethyl-1H-benzoimidazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-chloro-6-trifluoromethyl-1H-benzoimidazole (221 mg, 1 mmol, Example 1c), piperazine (172 mg, 2 mmol, Aldrich) and DMSO (2 mL) was stirred at 80° C. for 24 h. The mixture was cooled to room temperature, water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (2×5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 271 (M+1).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic phases were washed with water (2×5 mL) and brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

出典と根拠

ORDレコード
ord-e86feb2cc7564c5fb9120f920da27bee
出典データセット
uspto-grants-2009_09
特許番号
US07582761B2

反応ノート

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