Hydrochloric Acid → HCID 178478829, compound

HRID 2171724Notes

Reaction equation

HRID 2171724 reaction equation
[OH-].[Na+].[C:3]([NH:6][C:7]([NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][C:30]=4[Cl:39])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1)=[O:8])(=[NH:5])[NH2:4].C1COCC1.[ClH:45]>CCO>[ClH:39].[ClH:45].[C:3]([NH:6][C:7]([NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][C:30]=4[Cl:39])[CH2:27][CH2:28]3)=[N:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1)=[O:8])(=[NH:4])[NH2:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178498103HCID 178498103, compound

Product 1

HCID 178478829HCID 178478829, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1M aqueous NaOH solution was added to a mixture of methyl 4-{4-[5-(3-{[(carbamimidoylcarbamoyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}-3-chlorobenzoate (208 mg), THF (2 ml), and EtOH (2 ml), followed by stirring at room temperature for 2 hours. The reaction mixture was neutralized with 1M hydrochloric acid, and the precipitated solid was collected by filtration. A 4M hydrogen chloride/dioxane solution (1 ml) was added to a mixture of the obtained solid and dioxane (3 ml), followed by stirring at room temperature overnight. The insoluble matter was collected by filtration to obtain 4-{4-[5-(3-{[(carbamimidoylcarbamoyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}-3-chlorobenzoic acid dihydrochloride (112 mg).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. additionA 4M hydrogen chloride/dioxane solution (1 ml) was added to a mixture of the obtained solid and dioxane (3 ml)
  3. stirringby stirring at room temperature overnight
  4. filtrationThe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-ffc9cf13a8d246518fbc071a3f339e5e
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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