Phosphoric Acid → (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one hemiphosphate monohydrate

HRID 1875699Notes

Reaction equation

HRID 1875699 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]2[C:18]([CH:19]=1)=[C:17]([CH3:20])[CH:16]=[CH:15][CH:14]=2.[P:22](=[O:26])([OH:25])([OH:24])[OH:23]>C(O)C>[OH2:1].[P:22]([OH:26])([OH:25])([OH:24])=[O:23].[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]2[C:18]([CH:19]=1)=[C:17]([CH3:20])[CH:16]=[CH:15][CH:14]=2.[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]2[C:18]([CH:19]=1)=[C:17]([CH3:20])[CH:16]=[CH:15][CH:14]=2.[OH2:1]

Participants

4

Reactant 2

HCID 1004Phosphoric Acid2×HCID 10424118(R)-3-(2-(2-(hydroxymethyl)pyrrolidin-1-yl)ethyl)-5-methylisoquinolin-1(2H)-one

Product 1

HCID 131730055(R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one hemiphosphate monohydrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A free form (502 mg) of (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one was measured in a reaction test tube, aqueous ethanol (5.8 mL, ethanol:water=8:1) was added and the mixture was completely dissolved by heating under reflux. Thereto was added aqueous phosphoric acid solution (501 μL, solution prepared by diluting commercially available 85% phosphoric acid (2.02 g) with the above-mentioned aqueous ethanol to scale up to 10 mL), and the mixture was stirred at room temperature for one day and left standing. The precipitate was collected by filtration. The precipitate (301 mg) was measured in a reaction test tube, and aqueous ethanol (2.6 mL, ethanol:water=4:1) was added. The mixture was completely dissolved by heating under reflux, stirred at room temperature for one day and left standing. The precipitate was collected by filtration, and dried under reduced pressure at 50° C. for 5 hr to give the title compound (264 mg).

Workup

  1. dissolutionthe mixture was completely dissolved
  2. temperatureby heating
  3. temperatureunder reflux
  4. customprepared
  5. waitleft
  6. filtrationThe precipitate was collected by filtration
  7. customThe precipitate (301 mg) was measured in a reaction test tube
  8. additionaqueous ethanol (2.6 mL, ethanol:water=4:1) was added
  9. dissolutionThe mixture was completely dissolved
  10. temperatureby heating
  11. temperatureunder reflux
  12. stirringstirred at room temperature for one day
  13. waitleft
  14. filtrationThe precipitate was collected by filtration
  15. customdried under reduced pressure at 50° C. for 5 hr

Sources & evidence

ORD record
ord-dcbbf5c62a2b4f518fbbb8c86080128d
Source dataset
uspto-grants-2012_11
Patent number
US08309573B2

Reaction notes

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