Phosphoric Acid → HCID 86680545, compound

HRID 1472525Notes

Reaction equation

HRID 1472525 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].[P:27](=[O:31])([OH:30])([OH:29])[OH:28]>C(OC)(=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[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[F:21])[CH2:13][C:7]=2[CH:6]=1)=[O:3].[P:27]([O-:31])([O-:30])([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 6918456Prasugrel

Product 1

HCID 86680545HCID 86680545, compound

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of prasugrel base (1.006 g) in 21.67 ml of methyl acetate/7.7% ethanol at 20-25° C., a dropwise solution of 99% phosphoric acid (329.9 mg) in 2 ml of methyl acetate was added. Crystallization occurred within 30 minutes. After 3 hours at 20-25° C., the suspension was cooled to 0-5° C. and stirred for about 2 hours at that temperature. The obtained crystals were filtered, washed with 4 ml of methyl acetate and dried at 40° C./vacuum for about 1.5 hours. Prasugrel phosphate Form P1 (0.883 g) was obtained.

Workup

  1. customCrystallization
  2. waitAfter 3 hours at 20-25° C.
  3. filtrationThe obtained crystals were filtered
  4. washwashed with 4 ml of methyl acetate
  5. customdried at 40° C./vacuum for about 1.5 hours

Sources & evidence

ORD record
ord-671f73f6265946d5b66d825eecfae910
Source dataset
uspto-grants-2015_04
Patent number
US09012641B2

Reaction notes

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