HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 40193Generated: October 25, 2026
Triethylamine → 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine
https://huagongshe.com/reaction/40193
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N,N-Dimethylpropargylamine | HCID 81643 | — |
| Reactant | 4-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline | HCID 25066992 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ammonium hydroxide methanol | HCID 21894508 | — |
| Product | 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine | HCID 25065341 | 34.3% |
Reaction Steps
In a 10 mL sealed tube under N2 were dissolved dichlorobis(triphenylphosphine)palladium (41 mg, 59 μmol), N,N-dimethylprop-2-yn-1-amine (97 mg, 1170 μmol), 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (prepared according to General Method A) (200 mg, 585 μmol), TRIETHYLAMINE (1631 μl, 11704 μmol) and COPPER(I) IODIDE (11 mg, 59 μmol) in 3 mL of MeCN then stirred and heated at 80° C. for 10 h. The crude reaction mixture was directly purified by MPLC (ISCO) with DCM/DCM:MeOH:NH4OH (90:10:1) 95:5 to afforded 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylprop-2-yn-1-amine (26 mg, 11% yield) as a yellow solid. MS m/z=388.2 [M+1]+. Calc'd for C21H20N6O2: 389.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08524900B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-f4f499cd32ac4fcfab6ed56c723b95ac |
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| Source note | uspto-grants-2013_09 |
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