Hydrogen Bromide → Clopidogrel hydrobromide

HRID 887995Notes

Reaction equation

HRID 887995 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[BrH:22]>C(OC(C)C)(C)C>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH2:15][CH2:14]1)[C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[BrH:22]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 60606Clopidogrel

Product 1

HCID 11304210Clopidogrel hydrobromide

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
27.5 °C

Procedure

Clopidogrel (10 g) obtained from example 3 was dissolved in diisopropyl ether (129.3 ml) at 25-30° C. and 47% aqueous hydrobromic acid solution (3.79 ml) was added dropwise in 30 minutes at 25-30° C. The resulting suspension was stirred for 3 hours at 25-30° C. The resulting crude solid was filtered, washed with diisopropyl ether (10 ml) at 25-30° C. and dried under reduced pressure at 30-35° C. for 15 hours.

Workup

  1. filtrationThe resulting crude solid was filtered
  2. washwashed with diisopropyl ether (10 ml) at 25-30° C.
  3. customdried under reduced pressure at 30-35° C. for 15 hours

Sources & evidence

ORD record
ord-c6f876eff4b442a88247be4081b93fac
Source dataset
uspto-grants-2012_08
Patent number
US08247558B2

Reaction notes

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