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Cyclohexanecarboxylic acid → Fuzapladib

HRID 484096
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 484096
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 154529FuzapladibAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2503b772583445259e5feb32e26bb708
Quelldatensatz
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05229403

Notizen zur Reaktion

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