Hydrogen Bromide → Prasugrel hydrobroMide

HRID 2404960Notes

Reaction equation

HRID 2404960 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(O)CCC>[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 2631-ButanolSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Prasugrel base (0.51 g) was suspended in 5.0 ml of 1-butanol. A solution of 0.17 ml of 47% HBr (aq) in 2.5 ml of 1-butanol was added to form a clear solution. After 15 minutes at room temperature crystallization started. The resulting suspension was cooled to 0-5° C. and stirred for 1.5 hour. Crystals formed and were filtered, washed with 1-butanol and dried at 50° C./vacuum, yielding 0.53 g of prasugrel hydrobromide.

Workup

  1. customto form a clear solution
  2. customAfter 15 minutes at room temperature crystallization
  3. customCrystals formed
  4. filtrationwere filtered
  5. washwashed with 1-butanol
  6. customdried at 50° C./vacuum

Sources & evidence

ORD record
ord-d92b1909b50b42da93ae413aaff67b3e
Source dataset
uspto-grants-2014_08
Patent number
US08802854B2

Reaction notes

Loading…