Hydrogen Bromide → Prasugrel hydrobroMide

HRID 2404956Notes

Reaction equation

HRID 2404956 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

To a solution of prasugrel base (0.998 g) in acetone (16 ml) at 20-25° C. under nitrogen atmosphere was added dropwise a solution of 0.34 ml 47% HBr(aq) in 4 ml of acetone. Crystallization occurred during the addition. After 30 minutes, the resulting suspension was cooled down to 5-0° C. and stirred for 2 hours. Crystals were filtered off under a nitrogen atmosphere, washed with 6 ml of acetone ((4+2) ml in portions) and dried at 30° C./10 mbar for about 45 minutes. Form II of Prasugrel hydrobromide (1.269 g) was obtained.

Workup

  1. customCrystallization
  2. additionoccurred during the addition
  3. filtrationCrystals were filtered off under a nitrogen atmosphere
  4. washwashed with 6 ml of acetone ((4+2) ml in portions) and
  5. customdried at 30° C./10 mbar for about 45 minutes

Sources & evidence

ORD record
ord-574a506a1ece4f79a6905ae71c3f716a
Source dataset
uspto-grants-2014_08
Patent number
US08802854B2

Reaction notes

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