Pyridine → 3-benzoylamino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluoro-benzamide

HRID 1943123노트

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HRID 1943123 반응식
[NH2:1][C:2]1[C:3]([F:31])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]#[N:30])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH3:25])=[O:6].N1C=CC=CC=1.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1>[C:38]([NH:1][C:2]1[C:3]([F:31])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]#[N:30])[C:5]([NH:7][C:8]1[C:9]([CH3:25])=[CH:10][C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:17])[F:19])=[CH:12][C:13]=1[CH3:14])=[O:6])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chloride2회HCID 592269593-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluorobenzamide

생성물 1

HCID 592269643-benzoylamino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluoro-benzamide수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
140 °C

실험 절차

To a solution of 3-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluoro-benzamide (68 mg, 0.15 mmol) (Example I12) in tetrahydrofuran (2 ml) were added pyridine (36 μl, 0.45 mmol) and benzoyl chloride (21 μl, 0.18 mmol). The reaction mixture was heated in a microwave at 140° C. for 30 minutes. The reaction mixture was allowed to cool to ambient temperature. A second portion of benzoyl chloride (21 μl, 0.18 mmol) was added and heating repeated at 140° C. for 30 minutes. The reaction mixture was allowed to cool to ambient temperature and then partitioned between sodium hydrogen carbonate (1M) and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by reverse-phase chromatography (eluent: trifluoroacetic acid/water/acetonitrile 1:4:5 to 1:1:8) to give Compound No. D15 of Table D (0.024 g, 28% yield). 1H-NMR (400 MHz, CDCl3): 2.28 (6H, s), 7.33 (2H, s), 7.45-7.96 (9H, m) ppm.

후처리

  1. temperatureto cool to ambient temperature
  2. temperatureheating
  3. temperatureto cool to ambient temperature
  4. custompartitioned between sodium hydrogen carbonate (1M) and ethyl acetate
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by reverse-phase chromatography (eluent: trifluoroacetic acid/water/acetonitrile 1:4:5 to 1:1:8)
  9. customto give Compound No

출처 및 근거

ORD 기록
ord-3e4a57a47d664f9a875501da6c51da96
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389766B2

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