Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Cyclobutylcarbinol | HCID 78130 | — |
| Reactant | HCID 21897830 | HCID 21897830 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 21897708 | HCID 21897708 | 31% |
Reaction Steps
Di-imidazol-1-yl-methanone (0.25 mmol, 41 mg), and cyclobutyl methanol (0.25 mmol, 24 μL) were dissolved in DMSO (2 mL) and stirred for 30 minutes at room temperature. Then, 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (0.18 mmol, 80 mg) and triethylamine (0.54 mmol, 75 μL) were added. The mixture was heated in a microwave for 5 minutes at 120° C. The progress of the reaction was monitored by thin layer chromatography and LCMS. Purification by HPLC provided Compound A113 as a white solid (29 mg, 31%). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.71 (s, 1H); 8.22 (s, 1H); 7.87 (m, 3H); 4.37 (h, 1H); 4.00 (m, 4H); 3.16 (m, 2H); 3.05 (s, 3H); 2.56 (m, 1H); 2.12 (m, 2H); 2.01 (m, 2H); 1.85 (m, 2H); 1.73 (m, 4H). Exact mass calculated for C23H26FN5O4S2 519.61, found 520.3 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07132426B2 |
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| Source dataset | uspto-grants-2006_11 |
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| ORD ID | ord-23a06cd529a745c39ea66f84a25de55b |
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| Source note | uspto-grants-2006_11 |
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