Hydrochloric Acid → HCID 68107355, compound

HRID 2403583Notes

Reaction equation

HRID 2403583 reaction equation
[C:1]([O:5][C:6]([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[CH:43]=[CH:42][C:36]([C:37]([O:39]CC)=[O:38])=[CH:35][CH:34]=4)[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>CCO.C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[N:25][C:24]([N:27]3[CH2:28][CH2:29][N:30]([C:33]4[CH:43]=[CH:42][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=4)[CH2:31][CH2:32]3)=[N:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68106475HCID 68106475, compound

Product 1

HCID 68107355HCID 68107355, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate (451 mg) was dissolved in EtOH (5 ml) and THF (5 ml), and a 1 M aqueous NaOH solution (2 ml) was added thereto, followed by stirring at room temperature for 3 hours. After neutralization with 1 M hydrochloric acid (2 ml), water was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoic acid (269 mg).

Workup

  1. extractionfollowed by extraction with CHCl3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-6544409b0bfb4481b2bbbcccbc293ba6
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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