Triethylamine → HCID 57786125, 화합물

HRID 1399219노트

반응식

HRID 1399219 반응식
[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

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68771405HCID 68771405, 화합물

생성물 1

HCID 57786125HCID 57786125, 화합물수율 94.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bcfe13d452e94fd5badf7ca740d68fcb
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

반응 노트

불러오는 중…