Water → Ethyl 1-(2,2-difluoroethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243054노트

반응식

HRID 2243054 반응식
C[N:2]([CH3:20])[CH:3]=[C:4]([C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:21][CH:22]([F:25])CN.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[F:21][CH:22]([F:25])[CH2:20][N:2]1[C:12]2[C:11](=[CH:16][C:15]([I:17])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1362742,2-DifluoroethanamineHCID 58801734Ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate

생성물 1

HCID 59208381Ethyl 1-(2,2-difluoroethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (335 mg, 0.86 mmol) and 2,2-difluoroethylamine (76 mg, 0.94 mmol) in ethanol (3 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and dissolved in DMF (3 mL). Potassium carbonate (178 mg, 1.28 mmol) was added to the reaction mixture and the reaction was heated to 70° C. for 3 h, then cooled to room temperature and poured into water. The title compound formed a precipitate which was collected by filtration and placed upon lyophilizer overnight to remove residual water. MS (ESP): 408 (M+H+) for C14H12F2INO3; NMR: 1.29 (t, J=7 Hz, 3H), 4.25 (q, J=7 Hz, 2H), 4.96 (m, 2H), 6.50 (t, J=20 Hz, 1H), 7.73 (m, 1H), 8.08 (m, 1H), 8.50 (m, 1H), 8.70 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DMF (3 mL)
  3. temperaturethe reaction was heated to 70° C. for 3 h
  4. temperaturecooled to room temperature

출처 및 근거

ORD 기록
ord-ba5a3d2bba154d6fa2322e147ba64ecf
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674801B2

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