p-Toluenesulfonic acid monohydrate → LY-2584702 (tosylate salt)

HRID 2194484Notes

Reaction equation

HRID 2194484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:25]=[CH:24][N:23]=[C:22]5[NH:26][N:27]=[CH:28][C:21]=45)[CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>CO>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:25]=[CH:24][N:23]=[C:22]5[NH:26][N:27]=[CH:28][C:21]=45)[CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:29]([F:31])([F:30])[F:32]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 25118925Ly-2584702

Product 1

HCID 46205871LY-2584702 (tosylate salt)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a 1-L round bottom flask with overhead stirrer charge with 60.12 g of 4-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine (prepared according to either of the above preparations without the final salt formation step), followed by 250 mL of 5% aq. MeOH. Stir the resulting slurry and add p-toluenesulfonic acid monohydrate (26.88 g) followed by a rinse forward with the remaining 50 mL of 5% aq. MeOH. Stir the resulting slurry and cool the crystals to 5° C. After 1 h at 5° C., stop stirring and filter the slurry on a Buchner funnel Rinse the flask out with 75 mL of cold 5% aq. MeOH and use this rinse to wash the filter cake. Transfer the solids to a weighing dish and dry at 50° C. in vacuo all day and all night, with a slow air bleed. The final weight is 71.44 g.

Workup

  1. customprepared
  2. washa rinse forward with the remaining 50 mL of 5% aq. MeOH
  3. stirringStir the resulting slurry
  4. stirringstop stirring
  5. filtrationfilter the slurry on a Buchner funnel
  6. washRinse the flask out with 75 mL of cold 5% aq. MeOH
  7. washthis rinse
  8. washto wash the filter cake
  9. customdry at 50° C. in vacuo all day and all night, with a slow air

Sources & evidence

ORD record
ord-822b507695fe4c998585f2f6d0455c46
Source dataset
uspto-grants-2012_12
Patent number
US08334293B2

Reaction notes

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