Hydrogen Bromide → Prasugrel hydrobroMide

HRID 2404958Notes

Reaction equation

HRID 2404958 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×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 0.503 g of prasugrel base in 5 ml of methyl ethyl ketone at 20-25° C., was added dropwise a solution of 0.17 ml of 47% HBr (aq) in 2 ml of methyl ethyl ketone. Crystallization occurred at the end of the addition. After 2 hours, the resulting suspension was cooled down to 0-5° C. and stirred for about 30 minutes. The crystals that had formed were filtered off, washed with 1 ml of methyl ethyl ketone and dried at 40° C./10 mbar for about 3 hours. Prasugrel hydrobromide (0.595 g) was obtained.

Workup

  1. customCrystallization
  2. additionoccurred at the end of the addition
  3. customThe crystals that had formed
  4. filtrationwere filtered off
  5. washwashed with 1 ml of methyl ethyl ketone
  6. customdried at 40° C./10 mbar for about 3 hours

Sources & evidence

ORD record
ord-0599df052de948939ca98bee1c6b8883
Source dataset
uspto-grants-2014_08
Patent number
US08802854B2

Reaction notes

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