HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1802263Generated: October 31, 2026
Diisopropylethylamine → 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester
https://huagongshe.com/reaction/1802263
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | 4-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid | HCID 25247567 | — |
| Reactant | 2-(3-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine | HCID 67773981 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester | HCID 67776603 | 56% |
Reaction Steps
To a solution of 2-methyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester (8.0 g, 40.4 mmol) in DMF (120 ml) were added HATU (34 g, 88.9 mmol), 2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (10.6 g, 44.4 mmol) and DIPEA (30 ml, 161.1 mmol) at 0° C. The reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with water. The resultant precipitated solid was filtered, washed with water, dried azeotropically with toluene followed by vacuum to yield 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester as white solid (7.8 g, 56%). LC-MS: m/z=421.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08349824B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-64178b1d0fcc4844b497f065f3e0c146 |
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| Source note | uspto-grants-2013_01 |
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