HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylamine → methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylamine | HCID 6341 | — |
| 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-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid | HCID 68486211 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylate | HCID 68488034 | 41.2% |
Reaction Steps
To a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid (0.075 g, 0.368 mmol) in DMF (1 ml) was added DIPEA (0.193 ml, 1.105 mmol), HATU (0.168 g, 0.442 mmol), and ethyl amine (0.045 g, 0.553 mmol) and the reaction stirred at RT for 2 h. Purification was accomplished by HPLC to afford methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylate (0.035 g, 41% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s., 1H) 7.81 (t, 1H) 7.48 (d, 1H) 3.80 (s, 3H) 3.20 (dd, 2H) 1.08 (t, 3H). MS: m/z 231.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08304419B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-a3f2c04ec8b849c89c85bd5586e02ff2 |
| Source note | uspto-grants-2012_11 |