Hydrochloric Acid → HCID 67198201, compound

HRID 550797Notes

Reaction equation

HRID 550797 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[CH2:20][CH2:19]3)[C:12]3[CH2:17][CH2:16][CH2:15][C:13]=3[N:14]=2)=[C:4]([F:32])[CH:3]=1.[OH-].[Na+].Cl.Cl.CCOC(C)=O>C1COCC1.O.C1COCC1.CCO>[ClH:1].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:22][CH2:23]3)[C:12]3[CH2:17][CH2:16][CH2:15][C:13]=3[N:14]=2)=[C:4]([F:32])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 67196900HCID 67196900, compound

Product 1

HCID 67198201HCID 67198201, compoundYield 134.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 37.04 g ethyl 4-{1-[2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperidin-4-yl}butanoate, 160 ml of 1M aqueous sodium hydroxide, and 400 ml of THF-EtOH (1:1) was stirred at ambient temperature for 4 hours. To the reaction mixture, 160 ml of 1M hydrochloric acid aqueous solution and 700 ml of water were added, and the mixture was extracted twice with chloroform. The organic phase obtained was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The solid obtained was dissolved in 300 ml of THF, 50 ml of 4M HCl-EtOAc solution was added, the solution was concentrated under reduced pressure, and the resultant solid was recrystallized from water-acetonitrile to yield 25.35 g of 4-{1-[2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperidin-4-yl}butanoic acid hydrochloride.

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. customThe organic phase obtained
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe solid obtained
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resultant solid was recrystallized from water-acetonitrile

Sources & evidence

ORD record
ord-ee3c174d010e41f599ec93bf665742f2
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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