p-Toluenesulfonic acid monohydrate → 5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine

HRID 1842743

反応式

HRID 1842743 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)[C:5]([Cl:18])=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:31][C:32]1[C:38]([N+:39]([O-:41])=[O:40])=[CH:37][C:35]([NH2:36])=[C:34]([O:42][CH3:43])[CH:33]=1>CC(O)CCC>[Cl:18][C:5]1[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)=[N:7][C:2]([NH:36][C:35]2[CH:37]=[C:38]([N+:39]([O-:41])=[O:40])[C:32]([F:31])=[CH:33][C:34]=2[O:42][CH3:43])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 574290724-Fluoro-2-methoxy-5-nitroaniline2 回HCID 580714413-(2,5-Dichloropyrimidin-4-yl)-1-methyl-1H-indole2 回

生成物 1

HCID 712392825-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine収率 72.2%

試薬・触媒・溶媒 1

HCID 223862-Pentanol溶媒

反応条件

温度
125 °C

実験手順

A mixture of 3-(2,5-dichloropyrimidin-4-yl)-1-methylindole (Intermediate 88, 1281 mg, 4.60 mmol), p-toluene sulphonic acid monohydrate (964 mg, 5.07 mmol) and 4-fluoro-2-s methoxy-5-nitroaniline (Intermediate 23, 900 mg, 4.84 mmol) in 2-pentanol (50 mL) was heated at 125° C. for 18 h. A precipitate formed from the solution upon cooling. The precipitate was collected by filtration, washed with CH3OH (10 mL) and diethyl ether (20 mL) and dried on the filter to give the title compound (1.42 g, 72%) as a tan solid, which was used without further purification; 1H NMR: 3.91 (3H, s), 3.96 (3H, s), 7.05 (1H, t), 7.23-7.3 (1H, m), 7.39 (1H, d), 7.53 (1H, d), 8.33 (1H, d), 8.47 (1H, s), 8.58 (1H, s), 8.65 (1H, d), 8.76 (1H, s); m/z: ES+ MH+ 428.10.

後処理

  1. customA precipitate formed from the solution
  2. temperatureupon cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with CH3OH (10 mL) and diethyl ether (20 mL)
  5. customdried on the
  6. filtrationfilter

出典と根拠

ORDレコード
ord-7c385ee35133423b8d49db771377d6cb
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

関連ノート

読み込み中…