Pyridine → 3-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943092노트

반응식

HRID 1943092 반응식
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH2:20])[CH3:2].N1C=CC=CC=1.S(=[N:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])=O>ClCCl>[NH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([NH:20][C:4]1[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])=[CH:8][C:3]=1[CH2:1][CH3:2])=[O:34]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 12238911Benzoyl chloride, 3-(sulfinylamino)-HCID 227346102-Methyl-6-ethyl-4-(heptafluoro-prop-2-yl)-aniline

생성물 1

HCID 441994443-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (2.09 g, 6.9 mmol) (prepared according to EP 1,006,102) in dichloromethane (30 ml) under stirring at 25° C., was added sequentially pyridine (0.8 ml, 9.9 mmol) and a solution of 3-sulfinylamino-benzoyl chloride (1.39 g, 6.9 mmol) (Example 1.1) in dichloromethane (7 ml). The reaction mixture was stirred at ambient temperature for 6 hours. The reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml) and stirred vigorously for 20 minutes. The mixture was diluted with water (20 ml) and the phases separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2). After evaporation of the solvents, the yellow oil was triturated with hexane, where it crystallized. The desired compound was isolated as white crystals. M.p. 143-145° C. 1H-NMR as described for Example 3.1.

후처리

  1. customThe reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml)
  2. stirringstirred vigorously for 20 minutes
  3. additionThe mixture was diluted with water (20 ml)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. washThe combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2)
  10. customAfter evaporation of the solvents
  11. customthe yellow oil was triturated with hexane, where it
  12. customcrystallized

출처 및 근거

ORD 기록
ord-331a5f0311504c8f95227458b62d9b2d
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389767B2

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