Hydrazine hydrate (1:1) → 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

HRID 62064

반응식

HRID 62064 반응식
[F:1][C:2]([F:36])([F:35])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][N:24]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.O.NN>CO.ClCCl>[F:36][C:2]([F:1])([F:35])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 904048582-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)isoindoline-1,3-dione

생성물 1

HCID 904042683-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine수율 88%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

In a 100 mL flask, 2-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl) isoindoline-1,3-dione (2.50 g, 5.08 mmol) was diluted with methanol (25 mL). Hydrazine hydrate (0.740 mL, 15.2 mmol) was added and the reaction mixture was heated to 70° C. and stirred for 3 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane and washed with sodium hydroxide (1 N). The aqueous layer was further extracted with dichloromethane. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography using 50% ethyl acetate/petroleum ether as eluent to afford the title compound as white solid (1.60 g, 88%): mp 143-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.37 (s, 1H), 8.07 (d, J=9.2 Hz, 2H), 8.02 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.4 Hz, 2H), 7.34 (d, J=7.6 Hz, 2H), 2.66 (t, J=7.6 Hz, 2H), 2.56 (t, J=6.8 Hz, 2H), 1.90 (brs, 2H), 1.72-1.62 (m, 2H); ES+ m/z 363 ([M+H]+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with sodium hydroxide (1 N)
  3. extractionThe aqueous layer was further extracted with dichloromethane
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-6cc7de04489e4077a0359117239b270c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

연결된 노트

불러오는 중…