Triethylamine → HCID 21254744, 화합물

HRID 2287604노트

반응식

HRID 2287604 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]([N:16]([C:18]2[C:19]([Cl:39])=[C:20]([C:35]([Cl:38])=[CH:36][CH:37]=2)[CH2:21][O:22][C:23]2[C:31]3[N:30]=[C:29]([O:32][CH3:33])[N:28]([CH3:34])[C:27]=3[CH:26]=[CH:25][CH:24]=2)[CH3:17])=[O:15])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:48][C:49]1[C:54]([C:55](Cl)=[O:56])=[CH:53][CH:52]=[CH:51][N:50]=1>ClCCl>[Cl:39][C:19]1[C:18]([N:16]([CH3:17])[C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]2[CH:6]=[N:7][C:2]([NH:1][C:55]([C:54]3[C:49]([CH3:48])=[N:50][CH:51]=[CH:52][CH:53]=3)=[O:56])=[CH:3][CH:4]=2)=[CH:37][CH:36]=[C:35]([Cl:38])[C:20]=1[CH2:21][O:22][C:23]1[C:31]2[N:30]=[C:29]([O:32][CH3:33])[N:28]([CH3:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 183219202-Methylnicotinoyl chloride hydrochlorideHCID 21254648HCID 21254648, 화합물

생성물 1

HCID 21254744HCID 21254744, 화합물수율 81.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-[3-[N-[(E)-3-(6-aminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (100 mg) and triethylamine (53.3 mg) in dichloromethane (2 ml) was added 2-methyl-3-pyridinecarbonyl chloride hydrochloride (74.2 mg) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature and then for 3 hours at ambient temperature. The reaction mixture was concentrated, and the residue was dissolved in methanol (3 ml). To the solution was added 1N sodium hydroxide solution (0.5 ml), and the mixture was stirred for 1 hour. Chloroform was added to the reaction mixture, and the solution was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol, 10:1, v/v) to give 4-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(2-methylpyridin-3-carboxamido)pyridin-3-yl]acryloylglycyl]amino]benzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (99 mg).

후처리

  1. temperaturecooling
  2. waitfor 3 hours at ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in methanol (3 ml)
  5. additionTo the solution was added 1N sodium hydroxide solution (0.5 ml)
  6. stirringthe mixture was stirred for 1 hour
  7. additionChloroform was added to the reaction mixture
  8. washthe solution was washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by preparative thin layer chromatography (chloroform

출처 및 근거

ORD 기록
ord-324dd1129d3948c287c8b982004dc6cd
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083961

반응 노트

불러오는 중…