HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → methyl 2-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 1-Ethoxycarbonylcyclopropanecarboxylic acid | HCID 12510971 | — |
| Reactant | N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride | HCID 57505635 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | methyl 2-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropanecarboxylate | HCID 57505658 | 25% |
Reaction Steps
In the same manner as in Example 279 and using 2-(methoxycarbonyl)cyclopropanecarboxylic acid (140 mg, 0.78 mmol), tetrahydrofuran (1.5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (69 μL, 0.8 mmol), N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (250 mg, 0.6 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (75 mg, 25%) was obtained as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08044049B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-74cb6f5eaef643fc9efc1addd0d6504e |
| Source note | uspto-grants-2011_10 |