Ammonium Chloride → N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine

HRID 1842676ノート

反応式

HRID 1842676 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([N+:33]([O-])=O)[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([NH2:33])[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 71239353HCID 71239353、化合物2 回

生成物 1

HCID 86677326N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine収率 140.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 4-[1-(benzenesulfonyl)indol-3-yl]-5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]pyrimidin-2-amine (Intermediate 9, 349 mg, 0.47 mmol), iron (157 mg, 2.82 mmol) and NH4Cl (17.60 mg, 0.33 mmol) in ethanol (9 mL) and water (3 mL) was heated at reflux for 1.5 h. The mixture was cooled and concentrated in vacuo. CH2Cl2 (20 mL) and CH3OH (2 mL) were then added and the mixture was stirred for 5 minutes and then filtered. The organic solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (396 mg, 140%) as a green foam which was used without further purification. m/z: ES+ MH+ 601.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionCH2Cl2 (20 mL) and CH3OH (2 mL) were then added
  6. filtrationfiltered
  7. washThe organic solution was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-39656e78de5f4644ac38e7f2baaa35cf
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

反応ノート

読み込み中…