Acetone → Ticagrelor Succinate

HRID 589826Notes

Reaction equation

HRID 589826 reaction equation
[CH3:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[C:7]([NH:25][C@H:26]2[C@H:28]([C:29]3[CH:30]=[CH:31][C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[CH2:27]2)[C:8]2[N:13]=[N:12][N:11]([C@H:14]3[C@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([O:21][CH2:22][CH2:23][OH:24])[CH2:15]3)[C:9]=2[N:10]=1.CC(C)=O.[C:41]([OH:48])(=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45]>CCCCCC>[CH3:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[C:7]([NH:25][C@H:26]2[C@H:28]([C:29]3[CH:30]=[CH:31][C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[CH2:27]2)[C:8]2[N:13]=[N:12][N:11]([C@H:14]3[C@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([O:21][CH2:22][CH2:23][OH:24])[CH2:15]3)[C:9]=2[N:10]=1.[C:41]([O-:48])(=[O:47])[CH2:42][CH2:43][C:44]([O-:46])=[O:45]

Participants

5

Reactant 3

HCID 180AcetoneHCID 1110Succinic AcidHCID 9871419Ticagrelor

Product 1

HCID 131734467Ticagrelor SuccinateYield 81%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Ticagrelor (0.5 g) and acetone (10 mL) were charged into a round bottom flask and the mixture was stirred at about 25-30° C. for about 15 minutes for clear solution. Then succinic acid (0.12 g) was added to the above reaction mixture at 25-35° C. and stirred overnight. To the clear solution, n-hexane (50 mL) was added and stirred for about 90 minutes for solid separation. The solid was isolated by filtration, washed with n-hexane (5 mL) and dried to afford the title compound in about 81% yield having chiral HPLC purity of about 99%.

Workup

  1. stirringstirred overnight
  2. stirringstirred for about 90 minutes for solid separation
  3. customThe solid was isolated by filtration
  4. washwashed with n-hexane (5 mL)
  5. customdried

Sources & evidence

ORD record
ord-a4d6589e384c4ccd8df7c654c308b638
Source dataset
uspto-grants-2016_01
Patent number
US09233966B2

Reaction notes

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