HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 66692781, compound → HCID 178499437, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 66692781 | HCID 66692781 | — |
| Reactant | Methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate | HCID 86710849 | — |
| Reactant | HCID 178511742 | HCID 178511742 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178499437 | HCID 178499437 | 76.3% |
Reaction Steps
A suspension of methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate (438 mg, 1.75 mmol), trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine (463 mg, 1.995 mmol) and triazabicyclodecene (75 mg, 0.539 mmol) in THF (0.5 mL) was stirred in a sealed tube at room temperature for 18 hours. The reaction mixture was then transferred to a round bottomed flask using DCM as solvent and evaporated in vacuo to give yellow/brown gum which solidified (1.5 g). This material was dissolved in DCM and purified on silica (70 g) using a 0-100% ethyl acetate-cyclohexane gradient over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound as yellow crystals (601 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08754101B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-a549cc80c4ae4ae6bb9b0f27fce1d21a |
| Source note | uspto-grants-2014_06 |