Nitric Acid → HCID 44468843, compound

HRID 1472516Notes

Reaction equation

HRID 1472516 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].[N+:27]([O-:30])([OH:29])=[O:28].CCCCCCC>CC(C)=O>[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].[N+:27]([O-:30])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8900HeptaneHCID 6918456Prasugrel

Product 1

HCID 44468843HCID 44468843, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 251 mg of prasugrel base form I in 3.75 ml acetone at room temperature (20-25° C.), a solution of 50.6 l (1.1 eq) 65% aqueous nitric acid in 1.25 ml acetone was added in portions and the resulting mixture was stirred at room temperature for about 15 minutes. After addition of 5 ml heptane at 0-5° C. (ice bath), the clear reaction mixture turned to an emulsion (clear oil drops on the bottom of the flask). A white precipitate was obtained after storage for 17 hours at about −25° C. The mixture containing the precipitate was stirred for 1 hour at 0-5° C. (ice bath), filtered off, washed with 1 ml cold acetone/heptane (1:1) and dried at 40° C./10 mbar for about 2.5 hours. White crystals (269 mg) of prasugrel nitrate were obtained.

Workup

  1. customA white precipitate was obtained after storage for 17 hours at about −25° C
  2. additionThe mixture containing the precipitate
  3. stirringwas stirred for 1 hour at 0-5° C. (ice bath)
  4. filtrationfiltered off
  5. washwashed with 1 ml cold acetone/heptane (1:1)
  6. customdried at 40° C./10 mbar for about 2.5 hours

Sources & evidence

ORD record
ord-fc3de8e149514d738c3f72f7b292e45e
Source dataset
uspto-grants-2015_04
Patent number
US09012641B2

Reaction notes

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