Hydrochloric Acid → HCID 178478962, compound

HRID 419749Notes

Reaction equation

HRID 419749 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([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)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.CC(O)C.[ClH:35]>CC(C)=O>[ClH:35].[F:29][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([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)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178506148HCID 178506148, compound

Product 1

HCID 178478962HCID 178478962, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4 Charge 4-{4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine (442.9 g, 1.07 mol) along with IPA (4.43 L) and stir the resulting slurry at RT. Slowly add HCl (214 mL of a 5M aqueous solution, 1.07 mol, 1.0 eq) and heat to 50° C. Stir for 30 minutes and add acetone (4.43 L) and continue heating for 4 h. Cool to 15° C. for 2 hr then filter the solid. Wash the filter cake with acetone (800 mL) and dry resulting solid in vacuum oven at 60° C. for 3 h to afford the title compound (458 g, 94%) as a tan to off-white solid. M.p.=306° C.; MS (ES): m/z=414 [M+H]

Workup

  1. stirringStir for 30 minutes
  2. temperaturecontinue heating for 4 h
  3. temperatureCool to 15° C. for 2 hr
  4. filtrationthen filter the solid
  5. washWash the filter cake with acetone (800 mL)
  6. customdry
  7. customresulting solid in vacuum oven at 60° C. for 3 h

Sources & evidence

ORD record
ord-d826c323f687499fa1943e4b56242449
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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