Hydrogen Bromide → Prasugrel hydrobroMide

HRID 1472520Notes

Reaction equation

HRID 1472520 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(OC(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 7915Isopropyl AcetateSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 0.499 g of prasugrel base in 5.29 ml of isopropyl acetate/5.5% methanol at 20-25° C., was added dropwise a solution of 0.17 ml 47% HBr(aq) in 1.53 ml of isopropyl acetate/2% methanol. Crystallization occurred to form fluffy crystals. After 45 minutes the resulting suspension was cooled down to 0-5° C. and stirred for about 4 hours. The crystals were filtered off, washed with 1 ml of isopropyl acetate and dried at 40° C./10 mbar for about 17 hours. Prasugrel hydrobromide (0.553 g) was obtained.

Workup

  1. customCrystallization
  2. customto form fluffy crystals
  3. filtrationThe crystals were filtered off
  4. washwashed with 1 ml of isopropyl acetate
  5. customdried at 40° C./10 mbar for about 17 hours

Sources & evidence

ORD record
ord-f018d040a04044c7949f41035e341534
Source dataset
uspto-grants-2015_04
Patent number
US09012641B2

Reaction notes

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