HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Tetrafluoro-m-phenylenediamine dihydrochloride | HCID 149026 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 6-Bromopyrrolo(1,2-a)pyrazine-3-carboxylic acid hydrochloride | HCID 69713212 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide | HCID 10247203 | — |
Reaction Steps
To a suspension of 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylic acid hydrochloride (1.67 mmol), (R)-3-aminoquinulidine dihydrochloride (0.34 g, 1.67 mmol), DIEA (1.5 mL, 8.35 mmol) in DMF (20 mL) and THF (10 mL) is added HATU (0.64 g, 1.67 mmol). The resulting suspension is stirred for 16 h at which time it is concentrated to dryness under reduced pressure. The resulting material is absorbed to silica gel and purified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent) salted with fumeric acid, and crystallized from EtOH/acetone/Et2O to give an off white spheres. Yield 45%. HRMS (FAB) calcd. for C15H17BrN4O+H 349.0664, found 349.0647.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06858613B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-719641f08ec94b06a39361fb8608fa61 |
| Source note | uspto-grants-2005_02 |