Hydrochloric Acid → Prasugrel hydrochloride

HRID 1428167Notes

Reaction equation

HRID 1428167 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].[ClH: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[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[F:21])[CH2:13][C:7]=2[CH:6]=1)=[O:3].[ClH:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6918456Prasugrel

Product 1

HCID 10158453Prasugrel hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

Prasugrel free base prepared by example 3 (2.0 g) disclosed herein was dissolved in acetone (25 ml) with stirring at 20° C. until complete dissolution and the mixture was further stirred for 10 minutes. A solution of hydrochloric acid in acetone (0.46 ml hydrochloric acid (37 wt. %) dissolved in 5 ml acetone) was added slowly to the reaction mixture over 1 hour at 20° C. After the addition, a seed crystal (0.05 g) (crystalline form B2 of prasugrel hydrochloride), the resulting mixture was stirred at 20° C. for 15 hours followed by filtration. The obtained crystal was washed with acetone and dried under vacuum at 50° C. for 24 hours. The resulting product was prasugrel hydrochloride crystalline Form B2 with the HPLC purity of 99.74%. The yield was 90%.

Workup

  1. stirringthe mixture was further stirred for 10 minutes
  2. additionAfter the addition
  3. filtrationfollowed by filtration
  4. washThe obtained crystal was washed with acetone
  5. customdried under vacuum at 50° C. for 24 hours

Sources & evidence

ORD record
ord-8ea2865ae1c7402bbd5be984e4be41ce
Source dataset
uspto-grants-2015_01
Patent number
US08937053B2

Reaction notes

Loading…