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

HRID 77699

反応式

HRID 77699 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-deefaab6b7e44388a2959ca7d84573f4
出典データセット
uspto-grants-2014_09
特許番号
US08841318B2

関連ノート

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