Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 58504757 | HCID 58504757 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66991312 | HCID 66991312 | 5.3% |
Reaction Steps
A mixture of 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (650 mg, 2.14 mmol), cyclopropylamine (650 mg, 11.4 mmol), and Hunig's base (2 mL, 11.4 mmol) in 1,4-dioxane (5 mL) was heated for 2 hours at 120° C. in a BiotageInitiator® microwave synthesizer. Upon cooling, the mixture was decanted to remove the solids, and the resulting solution was concentrated to dryness. The crude material was purified by RPHPLC (gradient: 15% CH3CN/H2O to 45% CH3CN/H2O) to afford the title compound (32 mg) as a yellow solid. LC-MS (ES) m/z=282 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.46-0.49 (m, 2H), 0.73 (t, J=6.8 Hz, 2H), 2.62-2.67 (m, 1H), 5.37 (s, 2H), 6.0 (s, 2H), 6.38 (s, 1H), 7.02 (s, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.86 (s, 1H), 11.50 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08697685B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-cf9c18ee5aeb493ca12f61d5fbbbc836 |
|---|
| Source note | uspto-grants-2014_04 |
|---|