Maleic Acid → Prasugrel (Maleic acid)

HRID 2120714Notes

Reaction equation

HRID 2120714 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[C:9]([O:12][C:13]1[S:21][C:20]2[CH2:19][CH2:18][N:17]([CH:22]([C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[CH2:16][C:15]=2[CH:14]=1)(=[O:11])[CH3:10]>CC(C)=O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[C:9]([O:12][C:13]1[S:21][C:20]2[CH2:19][CH2:18][N:17]([CH:22]([C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[CH2:16][C:15]=2[CH:14]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 6918456Prasugrel

Product 1

HCID 9870150Prasugrel (Maleic acid)Yield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of maleic acid (932 g) in acetone (15 L) heated to 40° C. was added 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3000 g) obtained in Reference example 1. The mixture was stirred at room temperature for 2 hours. The resulting crystals were separated by filtration and washed with acetone (4 L) and then dried at 60° C. under reduced pressure for 8 hours to give the title compound as white crystals (3538 g, yield 90%)

Workup

  1. customobtained in Reference example 1
  2. customThe resulting crystals were separated by filtration
  3. washwashed with acetone (4 L)
  4. customdried at 60° C. under reduced pressure for 8 hours

Sources & evidence

ORD record
ord-cb3909cd38574883b0f6c06e30ceff5f
Source dataset
uspto-grants-2004_02
Patent number
US06693115B2

Reaction notes

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