Hydrogen Bromide → Prasugrel hydrobroMide

HRID 1472518Notes

Reaction equation

HRID 1472518 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

Prasugrel base (2.00 g) was dissolved in acetone (20 ml) at 20-25° C. A solution of 0.41 ml 47% HBr in 8 ml of acetone was added over 10 minutes. Crystallization took place immediately. The resulting suspension was stirred at 20-25° C. for 1.5 hours and than 2 hours at 5-0° C. Crystals formed and were filtered, washed with acetone and dried at 40° C./vacuum, yielding form II of prasugrel hydrobromide (1.75 g). HPLC purity: 99.67%.

Workup

  1. customCrystallization
  2. customCrystals formed
  3. filtrationwere filtered
  4. washwashed with acetone
  5. customdried at 40° C./vacuum

Sources & evidence

ORD record
ord-814ca63261f94f50aaa653d63c2ef629
Source dataset
uspto-grants-2015_04
Patent number
US09012641B2

Reaction notes

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