Hydrochloric Acid → Prasugrel hydrochloride

HRID 1428168Notes

Reaction equation

HRID 1428168 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]>O1CCCC1>[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 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prasugrel free base prepared by example 3 (2.3 g) disclosed herein was dissolved in tetrahydrofuran (30 ml) with stirring at room temperature until complete dissolution and the resulting mixture was further stirred for 10 minutes. A solution of hydrochloric acid in tetrahydrofuran (0.53 ml hydrochloric acid (37 wt. %) dissolved in 5 ml tetrahydrofuran) was added slowly to the resulting mixture over 1 hour at room temperature. The mixture was stirred at −5° C. for 15 hours followed by filtration. The obtained crystal was washed with tetrahydrofuran and dried under vacuum at 50° C. for 24 hours. The resulting product was prasugrel hydrochloride crystalline Form A. The yield was 98%.

Workup

  1. stirringthe resulting mixture was further stirred for 10 minutes
  2. stirringThe mixture was stirred at −5° C. for 15 hours
  3. filtrationfollowed by filtration
  4. washThe obtained crystal was washed with tetrahydrofuran
  5. customdried under vacuum at 50° C. for 24 hours

Sources & evidence

ORD record
ord-7c01ee57d41142cf8d588c27e8de01fc
Source dataset
uspto-grants-2015_01
Patent number
US08937053B2

Reaction notes

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