Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate | HCID 44607625 | — |
| Reactant | 4-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one | HCID 68194757 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 6-(2-chlorophenyl)-2-{[4-(pyrrolidin-2-yl)phenyl]amino}imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one | HCID 68195075 | — |
Reaction Steps
A mixture of Example 1E (0.048 g, 0.133 mmol) and tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate (0.056 g, 0.213 mmol) was heated in a capped vial at 130° C. for 30 minutes. The reaction mixture was treated with ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was dissolved in CH2Cl2 (2 mL) and treated with trifluoroacetic acid (0.103 ml, 1.334 mmol). The mixture was stirred at 35° C. overnight, concentrated, and purified by HPLC (see protocol in Example 1F) to provide the title compound as a trifluoroacetic acid salt. 1H NMR (500 MHz, CD3OD) δ 2.36-2.19 (m, 3H), 2.57-2.47 (m, 1H), 3.53-3.41 (m, 2H), 4.69-4.62 (m, 1H), 7.08 (d, J=1.9 Hz, 1H), 7.62-7.51 (m, 5H), 7.72-7.66 (m, 1H), 7.88 (d, J=1.9 Hz, 1H), 7.97-7.92 (m, 2H), 9.19 (s, 1H). MS (ESI+) m/z 458.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710065B2 |
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| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-75203152707547a486326d6a5da891be |
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| Source note | uspto-grants-2014_04 |
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