Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 44540963 | HCID 44540963 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dimethyl sulfoxide methanol | HCID 22036561 | — |
| Product | HCID 44540869 | HCID 44540869 | 2% |
Reaction Steps
To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.90 mmol, prepared as described in Example 18) in DMSO (14 ml). 2-Propanamine (0.022 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Further 2-propanamine (0.022 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, 2-propanamine (0.02 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time 2-propanamine (0.022 ml, 0.26 mmol) and DIPEA (0.113 ml) were both added to the mixture and it was heated at 160° C. for 2 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). The sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (2.1 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765743B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-b1c1066e1775496a9137e871b9e26314 |
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| Source note | uspto-grants-2014_07 |
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