HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → Tert-butyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Thieno[2,3-b]pyrazine-6-carboxylic acid | HCID 7164578 | — |
| 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 | 5-(Boc-amino)-2-methylaniline | HCID 24699786 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)phenylcarbamate | HCID 67125544 | 66.4% |
Reaction Steps
A solution of thieno[2,3-b]pyrazine-6-carboxylic acid (1.01 g, 5.61 mmol), HATU (1.8 g, 5.61 mmol) and DIPEA (1.953 mL, 11.21 mmol) in DMF (8 mL) was stirred for 15 min. (3-Amino-4-methyl-phenyl)-carbamic acid tert-butyl 27 (1.246 g, 5.61 mmol), DIPEA (1 eq) in DMF (8 mL) were added and stirred overnight at rt. Citric acid solution (3%) was added and extracted with EtOAc. Organic layer was washed with NaHCO3 solution, brine, dried and evaporated. Purification by chromatography (0-20% EtOAc in CH2Cl2) gave tert-butyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)phenylcarbamate 28 (1.43 g, 66.4%). (m/z)=385 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669256B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-c6783467ffb24d67982eabb77dea16fe |
| Source note | uspto-grants-2014_03 |