Hydrochloric Acid → HCID 68106306, compound

HRID 2403622Notes

Reaction equation

HRID 2403622 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[N:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])=[CH:35][C:34]=4[CH2:46][OH:47])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=O)(C)(C)C.[OH-].[Na+].[ClH:50]>CCO.C1COCC1>[ClH:50].[ClH:50].[NH2:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:28][CH2:29][N:30]([C:33]4[N:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:35][C:34]=4[CH2:46][OH:47])[CH2:31][CH2:32]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68107131HCID 68107131, compound

Product 1

HCID 68106306HCID 68106306, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-[6-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)-5-(hydroxymethyl)pyridin-3-yl]propanoate (222 mg) was dissolved in EtOH (1 ml) and THF (2 ml), and a 1 M aqueous NaOH solution (1 ml) was added thereto, followed by stirring at room temperature for 5 hours. To the reaction mixture was added 1 M hydrochloric acid (1 ml), and the solvent was evaporated under reduced pressure. To the obtained residue was added water, followed by extraction with CHCl3. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The product was dissolved in dioxane (2 ml), and 4 M hydrogen chloride/dioxane (0.8 ml) was added thereto. After stirring at room temperature overnight, the precipitated solid was collected by filtration to obtain 3-[6-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}-5-(hydroxymethyl)pyridin-3-yl]propionic acid dihydrochloride (203 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue was added water
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  7. dissolutionThe product was dissolved in dioxane (2 ml)
  8. addition4 M hydrogen chloride/dioxane (0.8 ml) was added
  9. stirringAfter stirring at room temperature overnight
  10. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-3e99e2431c494fad867dd565f03aa132
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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