HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | 1-Methylcyclopropanamine | HCID 11651149 | — |
| Reactant | 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid | HCID 86677897 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide | HCID 86678010 | 42.9% |
Reaction Steps
A mixture of 2-bromo-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (250 mg, 1.03 mmol), 1-methylcyclopropanamine (150 mg, 2.2 mmol) and HATU (456 mg, 1.2 mmol) in 20 mL of dry THF was stirred for 4 hours. The reaction mixture was evaporated to dryness, the residue suspended in 20 mL of 0.5 N HCl, product extracted with ethyl acetate (3×50 mL), organics combined dried with sodium sulfate, filtered and concentrated. The residue was triturated with petroleum ether (2 mL) then decanted and dried to give 2-bromo-N-isopropyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (125 mg, crude). LCMS: (M+H)+=285/287.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658646B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-a343c8ed0f1645549fc1b9aee109e545 |
| Source note | uspto-grants-2014_02 |