HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-(1,2,3,4-Tetrahydropyrazino[1,2-a]benzimidazol-8-yl)-4-[4-(trifluoromethyl)phenyl]pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate | HCID 68056088 | — |
| Product | 1-(1,2,3,4-Tetrahydropyrazino[1,2-a]benzimidazol-8-yl)-4-[4-(trifluoromethyl)phenyl]pyridin-2(1H)-one | HCID 57524760 | 53% |
Reaction Steps
tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate (15 mg, 0.023 mmol) was deprotected and converted to the hydrochloride according to Example 18 (step h) to provide the title compound (5 mg, 38%) as an orange solid: 1H NMR (500 MHz, DMSO-d6) δ 9.71 (s, 2H), 8.01 (d, J=8.3 Hz, 2H), 7.88 (d, J=8.3 Hz, 2H), 7.82 (d, J=7.8 Hz, 1H), 7.75 (m, 2H), 7.37 (d, J=8.4 Hz, 1H), 6.88 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 4.67 (s, 2H), 4.47-4.41 (m, 2H), 3.83-3.77 (m, 2H); ESI MS m/z 411 [M+H]+; HPLC (Method B) 91.3% (AUC), tR=12.8 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08993765B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-78675af589c3484c90883749fa7f6e3d |
| Source note | uspto-grants-2015_03 |