Pyridine → N-[2-Methyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-butyramide

HRID 602517노트

반응식

HRID 602517 반응식
C(OC(=O)[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.N1C=CC=CC=1.[C:34](Cl)(=[O:38])[CH2:35][CH2:36][CH3:37]>O1CCCC1.C(OCC)(=O)C>[CH3:26][C:21]1[CH:20]=[C:19]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=2)[CH:24]=[CH:23][C:22]=1[NH:25][C:34](=[O:38])[CH2:35][CH2:36][CH3:37]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 67266881(4-Amino-3-methylphenyl)-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester

생성물 1

HCID 67266732N-[2-Methyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-butyramide수율 49.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (4-amino-3-methylphenyl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (500 mg, 1.31 mmol) in dry tetrahydrofuran (10 mL) at 0° C. was added pyridine (159 mL, 1.97 mmol) followed by butyryl chloride (164 μL, 1.58 mmol) dropwise. After 5 minutes, the reaction mixture was allowed to warm to room temperature, and stirring was continued for 1 hour. The reaction mixture was then diluted with ethyl acetate, washed with 2 N HCl, saturated aqueous sodium bicarbonate twice, and brine, and was then dried over magnesium sulfate. Solvents were evaporated in vacuo and the residue was dissolved in a 1:1 mixture of dichloromethane and trifluoroacetic acid. After 30 minutes at room temperature the mixture was evaporated to dryness, the residue was dissolved in ethyl acetate (10 mL), the solution was washed twice with saturated aqueous sodium bicarbonate, twice with water, and was then dried over sodium sulfate. Evaporation of the solvents and recrystallization of the residue from ethyl acetate:heptane gave the title compound as a colorless solid (226 mg, 49%).

후처리

  1. waitwas continued for 1 hour
  2. washwashed with 2 N HCl, saturated aqueous sodium bicarbonate twice
  3. dry with materialbrine, and was then dried over magnesium sulfate
  4. customSolvents were evaporated in vacuo
  5. dissolutionthe residue was dissolved in a 1:1 mixture of dichloromethane and trifluoroacetic acid
  6. customAfter 30 minutes at room temperature the mixture was evaporated to dryness
  7. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
  8. washthe solution was washed twice with saturated aqueous sodium bicarbonate, twice with water
  9. dry with materialwas then dried over sodium sulfate
  10. customEvaporation of the solvents and recrystallization of the residue from ethyl acetate

출처 및 근거

ORD 기록
ord-915b18889b414430b5592ea460fad3e9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906537B2

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