Hydrogen Bromide → Prasugrel hydrobroMide

HRID 1472524Notes

Reaction equation

HRID 1472524 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].CO>C(OCCCC)(=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

5

Reactant 3

HCID 260Hydrogen BromideHCID 887MethanolHCID 6918456Prasugrel

Product 1

HCID 25071268Prasugrel hydrobroMide

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a suspension of prasugrel base (0.501 g) in 6.0 ml of n-butyl acetate at 20-25° C., a dropwise solution of 0.170 ml of 47% HBr(aq) in 1.0 ml of n-butyl acetate was added. After the first drop of the acid solution, 0.3 ml of methanol was added. After the addition, the suspension was stirred at 20-25° C. for about 30 minutes and cooled to 0-5° C. for about 2 hours. The obtained crystals were filtered, washed with 1 ml of n-butyl acetate and dried at 40° C./10 mbar for about 22 hours. Prasugrel hydrobromide form XIII was obtained (0.616).

Workup

  1. additionAfter the addition
  2. temperaturecooled to 0-5° C. for about 2 hours
  3. filtrationThe obtained crystals were filtered
  4. washwashed with 1 ml of n-butyl acetate
  5. customdried at 40° C./10 mbar for about 22 hours

Sources & evidence

ORD record
ord-4e300d7c8b5b4e0582f007a323d8007c
Source dataset
uspto-grants-2015_04
Patent number
US09012641B2

Reaction notes

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