Methanesulfonic Acid → N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

HRID 19494

反応式

HRID 19494 の反応式
C(O[CH:4](OCC)[CH2:5][N:6]=[C:7]=[NH:8])C.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18].CS(O)(=O)=O>C(O)C>[NH:19]1[CH:17]=[CH:16][N:8]=[C:7]1[NH:6][C:5]1[CH:4]=[C:13]([NH:19][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([C:13]([F:23])([F:24])[F:12])[CH:15]=2)[CH:14]=[CH:22][C:21]=1[CH3:20]

参加物

5

反応物 3

HCID 6395Methanesulfonic Acid2 回HCID 74535m-(Trifluoromethyl)benzamideHCID 10749464N-(2,2-diethoxyethyl)carbodiimide2 回

生成物 1

HCID 58973096N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of N-(2,2-diethoxyethyl)carbodiimide (398 mg, 2.51 mmol), 3-amino-4-methyl-phenyl]-3-trifluoromethyl-benzamide (649 mg, 2.20 mmol), methanesulfonic acid (143 μL, 2.20 mmol) in ethanol (25 mL) is heated at reflux for 16 hours. An additional portion of N-(2,2-diethoxyethyl)carbodiimide (525 mg, 3.32 mmol) and methanesulfonic acid (143 μL, 2.20 mmol) are added. After an additional 3 hours refluxing, the reaction mixture is concentrated. The residue is dissolved in HCl (6N, 5 mL) and ethanol (5 mL). After stirring overnight, the reaction mixture is concentrated and basified with 25% NaOH solution to a pH of 14. The mixture is stirred for 30 minutes, extracted with CH2Cl2, dried, concentrated and purified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%) to give the title compound.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter an additional 3 hours refluxing
  4. concentrationthe reaction mixture is concentrated
  5. dissolutionThe residue is dissolved in HCl (6N, 5 mL)
  6. concentrationthe reaction mixture is concentrated
  7. stirringThe mixture is stirred for 30 minutes
  8. extractionextracted with CH2Cl2
  9. customdried
  10. concentrationconcentrated
  11. custompurified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%)

出典と根拠

ORDレコード
ord-2b6863eb1d6b4541a5678bf5343bed44
出典データセット
uspto-grants-2010_06
特許番号
US07745437B2

関連ノート

読み込み中…