Hydrogen Bromide → Prasugrel hydrobroMide

HRID 2404959Notes

Reaction equation

HRID 2404959 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]>C(C(C)=O)C>[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 6569Methyl Ethyl KetoneSolvent2×

Procedure

Prasugrel base (5.00 g) was dissolved in 50.0 ml of methyl ethyl ketone. A solution of 1.7 ml of 47% HBr (aq) in 20 ml of methyl ethyl ketone was added. Prasugrel hydrobromide crystallized after 5 minutes. The resulting suspension was stirred at room temperature for 1 hour and then 0.5 hours at 0-5° C. The crystals that formed were filtered, washed with methyl ethyl ketone and dried at 50° C./vacuum, yielding 6.06 g of prasugrel hydrobromide.

Workup

  1. customPrasugrel hydrobromide crystallized after 5 minutes
  2. custom0.5 hours
  3. customat 0-5° C
  4. customThe crystals that formed
  5. filtrationwere filtered
  6. washwashed with methyl ethyl ketone
  7. customdried at 50° C./vacuum

Sources & evidence

ORD record
ord-1d268b80ce764a7e80a126b86bfc7a73
Source dataset
uspto-grants-2014_08
Patent number
US08802854B2

Reaction notes

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