Hydrogen Bromide → Prasugrel hydrobroMide

HRID 2404954Notes

Reaction equation

HRID 2404954 reaction equation
[CH3:1][C:2]([O:4][C:5]1[S:9][C:8]2[CH2:10][CH2:11][N:12]([CH:14]([C:22]([CH:24]3[CH2:26][CH2:25]3)=[O:23])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[F:21])[CH2:13][C:7]=2[CH:6]=1)=[O:3].[BrH:27]>CC(C)=O>[CH3:1][C:2]([O:4][C:5]1[S:9][C:8]2[CH2:10][CH2:11][N:12]([CH:14]([C:22]([CH:24]3[CH2:26][CH2:25]3)=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][C:7]=2[CH:6]=1)=[O:3].[BrH:27]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6918456Prasugrel

Product 1

HCID 25071268Prasugrel hydrobroMide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Prasugrel base (1.00 g) was dissolved in acetone (15.5 ml) at 20-25° C. Solution of 0.34 ml 47% HBr in 4.8 ml of acetone was added in solution of base. Clear solution was cooled down to 5-0° C. After 5 minutes crystallization took place. Suspension was stirred at 5-0° C. for 2 hours, filtered, crystals were washed with acetone and dried at 40° C./vacuum, yielding form II of prasugrel hydrobromide (1.26 g). HPLC purity: 99.94%.

Workup

  1. customAfter 5 minutes crystallization
  2. filtrationfiltered
  3. washcrystals were washed with acetone
  4. customdried at 40° C./vacuum

Sources & evidence

ORD record
ord-2ba14605e6fb4aa5b48c9ec1f55caf14
Source dataset
uspto-grants-2014_08
Patent number
US08802854B2

Reaction notes

Loading…