Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 90410174 | HCID 90410174 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 90410066 | HCID 90410066 | 29% |
Reaction Steps
To 2-chloro-7-(3,5-dimethylisoxazol-4-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazine (9.1 mg, 0.025 mmol) in N-methylpyrrolidinone (0.40 mL), triethylamine (10 μL, 0.075 mmol) and 2-propanamine (21.2 μL, 0.25 mmol) were added and the mixture was heated at 120° C. overnight. The mixture was diluted with MeOH and purified by preparative LCMS (pH 10) to give the desired compound (2.8 mg, 29%). 1H NMR (500 MHz, DMSO-d6): δ 7.29 (3H, m); 6.92 (3H, m); 6.78 (1H, m); 6.55 (1H, m); 5.80 (1H, s); 4.68 (1H, m); 4.45 (1H, m); 4.00 (1H, m); 2.20 (3H, s); 2.02 (3H, s); 1.20 (3H, m); 1.09 (3H, m). LCMS calc. for C23H25N4O2 (M+H)+: m/z=389.2. found: 389.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09227985B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-a4b8787bba0d4fd897bbb1f7a6aa024e |
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| Source note | uspto-grants-2016_01 |
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