Ammonia → (4-Bromo-2-chloro-phenyl)-[4-fluoro-6-(3H-imidazol-4-yl)-1H-benzoimidazol-5-yl]-amine

HRID 1176916ノート

反応式

HRID 1176916 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:23]([CH:24]3O[CH:27]=[N:26][CH:25]3S(C3C=CC(C)=CC=3)(=O)=O)=[CH:22][C:12]3[N:13](CCS(C)(=O)=O)[CH:14]=[N:15][C:11]=3[C:10]=2[F:39])=[C:4]([Cl:40])[CH:3]=1.[NH3:41]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:23]([C:24]3[NH:41][CH:27]=[N:26][CH:25]=3)=[CH:22][C:12]3[NH:13][CH:14]=[N:15][C:11]=3[C:10]=2[F:39])=[C:4]([Cl:40])[CH:3]=1

参加物

4

反応物 2

HCID 222AmmoniaHCID 21114188(4-Bromo-2-chloro-phenyl)-{4-fluoro-1-(2-methanesulfonyl-ethyl)-6-[4-(toluene-4-sulfonyl)-4,5-dihydro-oxazol-5-yl]-1H-benzoimidazol-5-yl}-amine

生成物 1

HCID 11463907(4-Bromo-2-chloro-phenyl)-[4-fluoro-6-(3H-imidazol-4-yl)-1H-benzoimidazol-5-yl]-amine収率 7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

(4-Bromo-2-chloro-phenyl)-{4-fluoro-1-(2-methanesulfonyl-ethyl)-6-[4-(toluene-4-sulfonyl)-4,5-dihydro-oxazol-5-yl]-1H-benzoimidazol-5-yl}-amine 10bb (0.072 g, 0.107 mmol) is treated with 2.4 mL of a 2.0 M NH3 in MeOH solution in a sealed pressure tube. The reaction mixture is then heated to 90° C. with stirring for 20 hours and furthered stirred at room temperature for 3 days. The reaction mixture is transferred to a round bottom flask and concentrated under reduced pressure. Purification by flash column chromatography, twice, eluted with 10:1 methylene chloride:MeOH, followed by successive trituations with methylene chloride and then diethyl ether gives 3 mg (7%) desired product: LC/MS ESI (+) m/z 408, 406 (M+ Br pattern) detected; 1H NMR (400 MHz, MeOH-d4)  8.23 (s, 1H), 7.87 (s, 1H), 7.74 (s, 1H), 7.46 (m, 1H), 7.32 (d, 1H), 7.05 (m, 1H), 6.20 (dd, 1H).

後処理

  1. stirringfurthered stirred at room temperature for 3 days
  2. customThe reaction mixture is transferred to a round bottom flask
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash column chromatography
  5. washtwice, eluted with 10:1 methylene chloride

出典と根拠

ORDレコード
ord-915304e80faa433f8dd95e74f98a4086
出典データセット
uspto-grants-2010_11
特許番号
US07842816B2

反応ノート

読み込み中…