4-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid dihydrochloride → JTV-803 free base

HRID 412527Notes

Reaction equation

HRID 412527 reaction equation
Cl.Cl.[C:3]([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH2:17][C:18]3([C:30]([OH:32])=[O:31])[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)=[CH:11][CH:12]=2)[CH2:7]1)(=[NH:5])[NH2:4]>O>[C:3]([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH2:17][C:18]3([C:30]([OH:32])=[O:31])[CH2:19][CH2:20][N:21]([C:24]4[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=4)[CH2:22][CH2:23]3)=[CH:11][CH:12]=2)[CH2:7]1)(=[NH:4])[NH2:5]

Participants

3

Reactant 1

HCID 111791494-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid dihydrochloride

Product 1

HCID 9844392JTV-803 free baseYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid dihydrochloride (11 g) was dissolved in water (100 ml) and filtrated. 4N Aqueous sodium hydroxide solution (20 ml) was added dropwise at 50° C., and the mixture was stirred at the same temperature for 30 min. After completion of the reaction, the resultant solid was collected by filtration, washed successively with water and ethanol, and dried under reduced pressure to give the title compound (7.7 g).

Workup

  1. filtrationfiltrated
  2. addition4N Aqueous sodium hydroxide solution (20 ml) was added dropwise at 50° C.
  3. customAfter completion of the reaction
  4. filtrationthe resultant solid was collected by filtration
  5. washwashed successively with water and ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5645012cdcd04472b4de9795a0731290
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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