Sodium Hydroxide → 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline

HRID 77699

반응식

HRID 77699 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C2C=CC=C(C(F)(F)F)C=2)=[CH:4][C:3]=1[C:21]1[CH:29]=[C:28]2[C:24]([C:25]3[CH:33]=[N:32][CH:31]=[N:30][C:26]=3[NH:27]2)=[CH:23][CH:22]=1.O1CCOCC1.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:21]1[CH:29]=[C:28]2[C:24]([C:25]3[CH:33]=[N:32][CH:31]=[N:30][C:26]=3[NH:27]2)=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 25152248N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-3-(trifluoromethyl)benzamide

생성물 1

HCID 690464994-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline수율 76.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-3-(trifluoromethyl)benzamide (442 mg, 0.990 mmol) was added 1,4-dioxane (2.0 mL) and water (2.0 mL) and sodium hydroxide (790 mg, 19.8 mmol). The resulting mixture was heated to 100° C. until LCMS indicated complete hydrolysis, typically 14-16 hours. The reaction was cooled to ambient temperature and the solvents were removed by evaporation. The residue was washed with water and the remaining solid was recovered by filtration, washed with additional water, and dried under reduced pressure to give the product (207 mg, 76%). 1H NMR (300 MHz, DMSO): δ 9.42 (s, 1H), 8.90 (s, 1H), 8.22 (d, 1H), 7.39 (s, 1H), 7.23 (d, 1H), 6.94 (d, 1H), 6.52 (m, 2H), 4.95 (s, 2H), 2.08 (s, 3H). MS (EI) m/z=275 (M+H).

후처리

  1. customhydrolysis, typically 14-16 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. customthe solvents were removed by evaporation
  4. washThe residue was washed with water
  5. filtrationthe remaining solid was recovered by filtration
  6. washwashed with additional water
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-deefaab6b7e44388a2959ca7d84573f4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

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