HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1184882Generated: November 1, 2026
Citric Acid → 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide
https://huagongshe.com/reaction/1184882
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,4-Difluoro-5-nitroaniline | HCID 2758312 | — |
| 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 | 7-Aminothieno[2,3-b]pyrazine-6-carboxylic acid | HCID 12225712 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide | HCID 67125705 | 48% |
Reaction Steps
A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (179 mg, 0.948 mmol), HATU and DIPEA (0.313 mL, 1.895 mmol) in DMF (6 mL) was stirred at rt for 15 min. 2,4-difluoro-5-nitroaniline 71 (165 mg, 0.948 mmol) was added and stirred overnight at 60° C. Citric acid solution (3%) was added and extracted with EtOAc. Organic layer was washed twice water, brine, dried and evaporated. Purification by chromatography (20% EtOAc in heptane) gave 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide 72 (157 mg, 48%). (m/z)=346 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08669256B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-beb35513b3834930b618bf8105fd54c5 |
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| Source note | uspto-grants-2014_03 |
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