Maleic Acid → Prasugrel (Maleic acid)

HRID 2120713Notes

Reaction equation

HRID 2120713 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 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of maleic acid (4.43 g) in acetone (60 ml) was added 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (15.0 g) obtained in Reference example 1, then the mixture was stirred at room temperature (25° C.) for 2 hours. The resulting crystals were separated by filtration and washed with a small amount of acetone and then dried at 50° C. under reduced pressure for 4 hours to give the title compound as white crystals (17.1 g, yield 92%)

Workup

  1. customobtained in Reference example 1
  2. customThe resulting crystals were separated by filtration
  3. washwashed with a small amount of acetone
  4. customdried at 50° C. under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-6f2a7f9e76894af28dbc1505340248eb
Source dataset
uspto-grants-2004_02
Patent number
US06693115B2

Reaction notes

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