Hydrochloric Acid → cis-(1S,2S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-propylsulfanyltriazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol;hydrochloride

HRID 589825Notes

Reaction equation

HRID 589825 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.[ClH:37]>C(OCC)(=O)C>[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]([CH:14]3[C@H:18]([OH:19])[C@H:17]([OH:20])[CH:16]([O:21][CH2:22][CH2:23][OH:24])[CH2:15]3)[C:9]=2[N:10]=1.[ClH:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9871419Ticagrelor

Product 1

HCID 91663279cis-(1S,2S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-propylsulfanyltriazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol;hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
27.5 °C

Procedure

Ticagrelor (0.5 g) and ethyl acetate (15 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 aqueous hydrochloric acid (0.12 mL, 35%) was added to the above reaction mixture at 25-35° C. and stirred for solid separation for about 2 hours. The solid was filtered, washed with ethyl acetate (5 mL) and dried to afford the title compound in about 75% yield having chiral HPLC purity of 99.55%.

Workup

  1. stirringstirred for solid separation for about 2 hours
  2. filtrationThe solid was filtered
  3. washwashed with ethyl acetate (5 mL)
  4. customdried

Sources & evidence

ORD record
ord-b7d2e52becbf43bdaa871f1c83d1da03
Source dataset
uspto-grants-2016_01
Patent number
US09233966B2

Reaction notes

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