HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → azanium (2E)-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(4-pyridin-2-yltriazol-1-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethynylpyridine | HCID 137268 | — |
| Reactant | (2E)-3-azido-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]propanoic acid | HCID 89676234 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | azanium (2E)-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(4-pyridin-2-yltriazol-1-yl)propanoate | HCID 140611604 | — |
Reaction Steps
KY-767-batch-A To a solution of (E)-3-azido-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono) propanoic acid (E)-KY-757, (100 mg) in CH3CN 1 ml, tert-butanol 0.4 ml was added diisopropylethylamine 96 ul followed by 2-ethynylpyridine (0.4 mmol, 41 ul), CuI (15 mg). The reaction stirred at rt for 3 h. LC-MS assay showed two isomers. The solvent was removed under pressure. The residue was purified on C18 reversed phase flash chromatography column employing a linear gradient of 0-30% A in B (flow rate 40 ml/min), were A is 10% NH4OH in CH3CN and B is water, yielding (14 mg, 18%) of pure (E)-KY-788. MS+(ESI) m/z 373.91, calcd mass 473.85.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08969573B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-90458f3d685c4de9a906d43a869ecd24 |
| Source note | uspto-grants-2015_03 |