Fumaric Acid → (R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine Fumaric Acid Salt

HRID 1694576Notes

Reaction equation

HRID 1694576 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH2:2]1.[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>C(OC(C)C)(=O)C.C(O)C>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH2:2]1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 44594455(R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine

Product 1

HCID 44594457(R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine Fumaric Acid SaltYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7915Isopropyl AcetateSolvent

Procedure

To the solution of (R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine in isopropyl acetate (5.0 mL, 65 mg/mL by HPLC, from Example 3) was added 6.1 mL of 0.25 M fumaric acid in ethanol. The mixture was stirred until a slurry was formed. The suspension was filtered, washed with ethanol, and dried in a vacuum oven at 60° C. (R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine fumaric acid salt was obtained as a yellow solid (440 mg, 84% yield).

Workup

  1. customwas formed
  2. filtrationThe suspension was filtered
  3. washwashed with ethanol
  4. dry with materialdried in a vacuum oven at 60° C. (R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine fumaric acid salt

Sources & evidence

ORD record
ord-4aa7d44b43e14fd5b1691f06a6107626
Source dataset
uspto-grants-2012_04
Patent number
US08158796B2

Reaction notes

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