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Cyclohexanecarboxylic acid → Fuzapladib

HRID 484096
Notes
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Reaction equation

HRID 484096 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 154529FuzapladibYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2503b772583445259e5feb32e26bb708
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05229403

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes