N-[2-[N-ethyl-N-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → n-[2-[n-Ethyl-n-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-[2-[N-ethyl-N-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide | HCID 44183580 | — |
| Reactant | n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt | HCID 52952259 | — |
| Product | n-[2-[n-Ethyl-n-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt | HCID 52952368 | 80% |
Reaction Steps
This compound was prepared, starting from compound 16 (251 mg, 0.49 mmol), according to the procedure developed for compound 11 to give compound 17 (231 mg, 0.40 mmol) as a very hygroscopic yellow solid. Yield 80%; mp 99-101° C. (dec.); IR (KBr) ν 1163, 1225, 1421, 1474, 1522, 1622, 1670, 2500-2800, 2850-3000, 3100-3600 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, 3H, J=7.0 Hz), 3.33 (q, 2H, J=6.6 Hz), 3.62 (m, 2H), 3.80 (m, 6H), 6.12 (dd, 1H, J=2.0, 8.0 Hz), 6.40 (dd, 1H, J=2.0, 8.0 Hz), 7.30 (se, 1H), 7.50 (q, 1H, 4JH-F=8.0 Hz, J=8.0 Hz), 7.92 (d, 1H, J=8.8 Hz), 8.25 (dd, 1H, J=1.8, 8.8 Hz), 8.64 (d, 1H, J=1.6 Hz), 9.38 (t, 1H, J=6.0 Hz), 9.44 (s, 1H), 10.28 (se, 1H); ESI-MS m/z 509.1 [M+H]+; Anal. Calcd for C20H22OIN6F, 2HCl: C, 41.33; H, 4.16; N, 14.46. Found: C, 43.19; H, 4.31; N, 14.74.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09125937B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-f03788cf4ae04ed192af78a630b8dc37 |
| Source note | uspto-grants-2015_09 |