HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrogen Bromide → 4-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| Reactant | 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide | HCID 57590054 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 4-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamide | HCID 59023028 | 41.7% |
Reaction Steps
5,8-dibromoimidazo[1,2-a]pyrazine (285 mg, 1.03 mmol) and 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide (280 mg, 1.03 mmol) are stirred in iPrOH (5 mL) and HBr (48% aq., 380 μL) is added. The mixture is heated at reflux for 24 hours. The cooled suspension is poured into NaHCO3 (sat. aq., 25 mL) and water (25 mL) and extracted with CHCl3 (3×40 mL). The extracts are dried over MgSO4 and evaporated. The residue is purified by column chromatography, eluting with 10%-20% DCM/MeOH to afford the title compound as a pale yellow solid (200 mg, 0.43 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173656B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-0b563f095e134b25b9f2a49412808ad2 |
| Source note | uspto-grants-2012_05 |