Triethylamine → HCID 57786125、化合物

HRID 1628865ノート

反応式

HRID 1628865 の反応式
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[Cl:20])[N:7]([CH2:21][CH2:22][CH2:23][CH2:24]O)[C:6]=2[C:5](C(OC)=O)=[CH:4][CH:3]=1.[CH2:30](N(CC)CC)C.CS(Cl)(=O)=O.[C:42](=[O:45])([O-])[O-:43].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:42]([O:43][CH3:30])=[O:45])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[Cl:20])[CH2:24][CH2:23][CH2:22][CH2:21][N:7]21

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68771405HCID 68771405、化合物

生成物 1

HCID 57786125HCID 57786125、化合物収率 94.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

To a stirred solution of methyl 4-chloro-2-[(2-chloro-4-methoxyphenyl)amino]-1-(4-hydroxybutyl)-1H-benzimidazole-7-carboxylate (Reference example 169, 1.31 g, 2.98 mmol) and triethylamine (1.04 mL, 7.45 mmol) in tetrahydrofuran (15 mL) was added methanesulfonyl chloride (277 μL, 3.58 mol) at 0° C. After 15 min, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (30 mL) and potassium carbonate (1.24 g, 8.94 mmol) was added. After being stirred for 1 h at 80° C., the reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting solid was washed with diisopropyl ether to give the title compound as a colorless solid (1.18 g, 2.81 mmol, 94%).

後処理

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (30 mL)
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washThe resulting solid was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-0bec29aeccef4a589b999455f4435dad
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

読み込み中…