Triethylamine → 10-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2244195노트

반응식

HRID 2244195 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].C(Cl)(=O)C(Cl)=O.[CH:25]1[CH:26]=[CH:27][N:28]2[CH2:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[NH:31][CH2:30][C:29]=12.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:31]2[C:32]3[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=3[CH2:34][N:28]3[CH:27]=[CH:26][CH:25]=[C:29]3[CH2:30]2)=[O:11])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 180010763-Methoxy-4-(2-methylphenyl)benzoic acid

생성물 1

HCID 6867947010-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine수율 95%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-methoxy-2′-methyl-biphenyl-4-carboxylic acid of Step D (23 mmol) in dichloromethane (50 mL) was added a drop of N,N-dimethylformamide. Oxalyl chloride (36 mmol) was then added dropwise to the solution. The solution was then stirred at reflux temperature for 2 hours. The solvents were evaporated and the resulting acid chloride was dissolved in 20 mL dichloromethane. This was added dropwise to a stirred mixture of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (25 mmol), and triethylamine (34 mmol) in dichloromethane (30 mL) at 0° C. under nitrogen atmosphere. After 20 hours the mixture was quenched with water and washed with 0.5 N hydrochloric acid, 1.0 N sodium hydroxide, and brine. The solution was dried over anhydrous sodium sulfate, and evaporated to a solid. The product was purified by column chromatography using ethyl acetate and hexane (1:3) to provide 8.77 g (95%) of the title compound as a white solid.

후처리

  1. temperatureat reflux temperature for 2 hours
  2. customThe solvents were evaporated
  3. dissolutionthe resulting acid chloride was dissolved in 20 mL dichloromethane
  4. customAfter 20 hours the mixture was quenched with water
  5. washwashed with 0.5 N hydrochloric acid, 1.0 N sodium hydroxide, and brine
  6. dry with materialThe solution was dried over anhydrous sodium sulfate
  7. customevaporated to a solid
  8. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-1af4ab16ef7446b1826dfd0f4b954cc1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678787B2

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