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

HRID 19494

반응식

HRID 19494 반응식
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]

참가 물질

5

반응물 3

HCID 6395Methanesulfonic Acid2회HCID 74535m-(Trifluoromethyl)benzamideHCID 10749464N-(2,2-diethoxyethyl)carbodiimide2회

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-2b6863eb1d6b4541a5678bf5343bed44
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745437B2

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