HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1055992Generated: October 26, 2026
Diisopropylethylamine → N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide
https://huagongshe.com/reaction/1055992
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloropyridine-3,4-diamine | HCID 285736 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-Phenoxyquinoline-8-carboxylic acid | HCID 89782088 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide | HCID 89782020 | — |
| Product | N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide | HCID 89782144 | — |
Reaction Steps
A mixture of 2-phenoxyquinoline-8-carboxylic acid (119 mg, 0.449 mmol), 2-chloropyridine-3,4-diamine (97 mg, 0.673 mmol, Waterstone Technology, Carmel, Ind.), HATU (341 mg, 0.897 mmol), and DIPEA (235 μl, 1.346 mmol) in DMF (449 μl) was stirred at RT for 2 h. The mixture was diluted with EtOAc (100 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (3×75 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica chromatography (100% DCM to 5% MeOH/DCM) provided N-(3-amino-2-chloropyridin-4-yl)-2-phenoxyquinoline-8-carboxamide (or N-(4-amino-2-chloropyridin-3-yl)-2-phenoxyquinoline-8-carboxamide; regioisomer not determined; 178d, 49% yield). MS (ESI, pos. ion) m/z: 391.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09394297B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-8ac49400164d4853ab290c11952e5d11 |
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| Source note | uspto-grants-2016_07 |
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