Isopropanol → HCID 178488776, compound

HRID 419742Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[NH:22][CH:23]=2)=[CH:15][CH:14]=1.C(O)(C)C.C(N(C(C)C)CC)(C)C>CO.C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH:24]3[CH2:29][CH2:28][N:27]([C:2]4[N:7]=[CH:6][N:5]=[C:4]5[NH:8][N:9]=[CH:10][C:3]=45)[CH2:26][CH2:25]3)[NH:22][CH:23]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Place 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (135 mg; 1.10 equiv; 873.45 μmoles) and 4-[4-(4-Methoxy-phenyl)-1H-imidazol-2-yl]-piperidine (205 mg, 1.00 equiv; 796.63 μmoles; 205.00 mg) in a microwave vial and dissolve in isopropyl alcohol (3 mL; 39.24 mmoles; 3.00 mL). Add diisopropylethylamine (0.5 mL; 2.87 mmoles; 500.00 μL). Heat the mixture to 70° C. in a microwave with stirring on and hold for 1 hr. Dissolve in 5% MeOH/DCM and wash with saturated aqueous sodium bicarbonate. Dry over sodium sulfate, filter and concentrated. 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. over 35 min collection. Combine the fractions to give 4-{4-[4-(4-Methoxy-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine.

Workup

washwash with saturated aqueous sodium bicarbonate
dry with materialDry over sodium sulfate
filtrationfilter
concentrationconcentrated
customPurify
washeluting with a gradient of 2.5% MeOH/DCM to 10% MeOH/DCM at a flow rate of 40 mL/min. over 35 min
customcollection

Sources & evidence

ORD record: ord-26e0267df13a4afcbfa29b13e15f6e72
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093383B2

Reaction notes

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