Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one | HCID 89783320 | — |
| Product | HCID 71731145 | HCID 71731145 | 78% |
Reaction Steps
Prepared similarly to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 55 mg, 0.186 mmol) and cyclopropanamine (25.7 μl, 0.371 mmol, Aldrich), heating at 100° C. for 30 min. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (78% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70-0.75 (m, 2H) 0.96 (dd, J=6.65, 1.96 Hz, 2H) 2.56 (s, 3H) 2.86-2.96 (m, 3H) 3.44 (td, J=6.80, 2.25 Hz, 2H) 6.98 (br. s., 1H) 7.16 (d, J=2.15 Hz, 1H) 7.37 (t, J=7.82 Hz, 1H) 7.58 (d, J=1.17 Hz, 2H) 7.99 (dd, J=7.63, 1.17 Hz, 1H) 12.83 (br. s., 1H). MS (ESI, pos. ion) m/z: 334.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09394297B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-c7ab457e25cd42348028e39b33ea90ff |
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| Source note | uspto-grants-2016_07 |
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