Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one | HCID 89783320 | — |
| Product | HCID 89784273 | HCID 89784273 | 47% |
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; 45 mg, 0.152 mmol) and propan-2-amine (38.8 μl, 0.456 mmol, Aldrich), heating at 100° C. for 30 min. Purification by silica gel (100% DCM to 3% MeOH/DCM) provided 2-(3-(isopropylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4 (5H)-one (47% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (d, J=6.46 Hz, 6H) 2.56 (s, 3H) 2.90 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.80, 2.25 Hz, 2H) 4.30 (dq, J=13.23, 6.48 Hz, 1H) 6.88 (d, J=7.04 Hz, 1H) 6.96 (br. s., 1H) 7.12 (s, 1H) 7.33 (t, J=7.82 Hz, 1H) 7.57 (dd, J=7.92, 1.27 Hz, 1H) 7.90 (dd, J=7.63, 1.17 Hz, 1H) 12.23 (br. s., 1H). MS (ESI, pos. ion) m/z: 336.0 (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-c40a896ae6134deaaf7ce8a580b75d20 |
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| Source note | uspto-grants-2016_07 |
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