Isopropanol → HCID 178526600, compound

HRID 419743Notes

Reaction equation

HRID 419743 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.Cl.[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[N:22]=[C:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[NH:24][CH:25]=2)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(O)(C)C.C(N(C(C)C)CC)(C)C>>[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[N:22]=[C:23]([CH:26]3[CH2:31][CH2:30][N:29]([C:2]4[N:7]=[CH:6][N:5]=[C:4]5[NH:8][N:9]=[CH:10][C:3]=45)[CH2:28][CH2:27]3)[NH:24][CH:25]=2)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 178479769HCID 178479769, compound

Product 1

HCID 178526600HCID 178526600, compound

Conditions

Temperature
70 °C

Procedure

Place 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (150 mg; 1.16 equiv; 970.50 μmoles; 150.00 mg), and 4-[4-(3-Nitro-phenyl)-1H-imidazol-2-yl]-piperidine hydrochloride salt (258 mg 1.00 equiv; 835.58 μmoles; 258.00 mg) in a microwave vial and dissolve in isopropyl alcohol (3 mL; 39.24 mmoles; 3.00 mL) and add diisopropylethylamine (0.5 mL; 2.87 mmoles; 500.00 μL). Heat the mixture to 70° C. in a Emrys Optimizer microwave for 1 hour while stirring. Filter, and concentrate filtrate to an oil. Combine solid and oil and dissolve in 3% MeOH/DCM. Purify using ISCO chromatography over a biotage 40S column eluting with a gradient of 2.5% MeOH/DCM to 10% MeOH/DCM at a flow rate of 40 mL/min. Collect appropriate fractions, concentrate to an oil. Dissolve oil in 10% MeOH/DCM and wash with a mixture of aqueous sodium bicarbonate/saturated aqueous sodium chloride three times. Wash the combined organic layers with saturated aqueous sodium chloride and dry over sodium sulfate. Concentrate and dry under reduced pressure to obtain the title compound.

Workup

  1. filtrationFilter
  2. concentrationconcentrate filtrate to an oil
  3. dissolutionCombine solid and oil and dissolve in 3% MeOH/DCM
  4. customPurify
  5. washeluting with a gradient of 2.5% MeOH/DCM to 10% MeOH/DCM at a flow rate of 40 mL/min
  6. customCollect appropriate fractions
  7. concentrationconcentrate to an oil
  8. dissolutionDissolve oil in 10% MeOH/DCM
  9. washwash with a mixture of aqueous sodium bicarbonate/saturated aqueous sodium chloride three times
  10. washWash the combined organic layers with saturated aqueous sodium chloride
  11. dry with materialdry over sodium sulfate
  12. concentrationConcentrate
  13. customdry under reduced pressure

Sources & evidence

ORD record
ord-c4b9ee91d0f54ff0a10acd46c8905f86
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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