Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | 4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine | HCID 58083234 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 46220330 | HCID 46220330 | 11.7% |
Reaction Steps
A solution of 4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (0.04 g, 0.14 mmol) in acetonitrile (2 mL) was treated with propylamine (0.041 g, 0.7 mmol) in the presence of p-toluenesulfonic acid monohydrate (0.03 g, 0.14 mmol). The reaction mixture was heated at 190° C. in microwave for 2 h. Solvent were removed and the crude material was purified by mass directed purification to obtain 5 mg of 103 as a white solid. 1H NMR (400 MHz, MeOD) δ 8.57 (s, 1H), 8.11 (d, J=1.2, 1H), 7.63 (t, J=7.4, 2H), 7.50 (t, J=7.2, 1H), 6.72 (s, 1H), 4.04 (t, J=22.1, 3H), 3.40 (dd, J=20.2, 13.0, 2H), 1.79 (dd, J=14.5, 7.1, 2H), 1.07 (t, J=7.4, 3H). MS (ESI) m/z 307.2 (M+1)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08653098B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-38133aff4e6c499684b582a1729eac4f |
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| Source note | uspto-grants-2014_02 |
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