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Cyclohexanecarboxylic acid → Fuzapladib

HRID 484096
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인쇄 미리보기

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HRID 484096 반응식
Cl.C(N=C=NCCCN(C)C)C.[NH2:13][C:14]1[C:15]([NH:24][S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.[CH:30]1([C:36](O)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[CH2:28]([S:25]([NH:24][C:15]1[C:14]([NH:13][C:36]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:37])=[CH:19][C:18]([C:20]([F:23])([F:21])[F:22])=[CH:17][N:16]=1)(=[O:27])=[O:26])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7413Cyclohexanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10730665N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide

생성물 1

HCID 154529Fuzapladib수율 62.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

An alternative process will be described. In 20 ml of methylene chloride, 0.5 g of 4-diemthylaminopyridine was dissolved, and 0.78 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and dissolved. Then, 1 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide was added thereto, and 30 minutes later, 0.52 g of cyclohexane-carboxylic acid was added thereto, and stirring was conducted for 10 hours. After completion of the reaction, 40 ml of methylene chloride was added to the reaction product, and the reaction product was washed with 10% hydrochloric acid and then washed with an aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. From the extract layer, solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 0.88 g of the desired product.

후처리

  1. dissolutiondissolved
  2. additionwas added to the reaction product
  3. washthe reaction product was washed with 10% hydrochloric acid
  4. washwashed with an aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationFrom the extract layer, solvent was distilled off
  7. customthe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2503b772583445259e5feb32e26bb708
출처 데이터셋
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05229403

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