Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | tert-butyl 6-oxo-1,2,4a,5,6,7-hexahydropyrazino[1,2-a][1,5]benzodiazepine-3(4H)-carboxylate | HCID 58284919 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Product | HCID 49764679 | HCID 49764679 | — |
Reaction Steps
Formalin solution (0.3 mL, 3.92 mmol) was added to a solution of the product of Example 22D (150 mg, 0.473 mmol) in 88% formic acid (4 mL), and the solution was stirred at 100° C. under nitrogen for 30 minutes. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by chromatography (SiO2, eluted with CH2Cl2-methanol-15 M NH4OH, 90:10:1) to provide the title compound: 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 2.05 (d, J=12.8 Hz, 1H), 2.66 (dd, J=13.6, 7.2 Hz, 1H), 2.90 (s, 3H), 3.08-3.19 (m, 2H), 3.32-3.39 (m, 2H), 3.53 (t, J=11.0 Hz, 2H), 3.57-3.67 (m, 1H), 7.00-7.04 (m, 1H), 7.08-7.13 (m, 1H), 7.13-7.18 (m, 1H), 7.18-7.24 (m, 1H); MS (DCI) m/z 232 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133206B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-9cd0d9bf442d44b68be05b62a30c4f27 |
|---|
| Source note | uspto-grants-2015_09 |
|---|
