HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 59406925, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| 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 | 3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid | HCID 25137682 | — |
| Reactant | HCID 131730313 | HCID 131730313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59406925 | HCID 59406925 | 100.1% |
Reaction Steps
3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 1; 304 mg) was dissolved in anhydrous DMF. HATU (596 mg), HOAT (213 mg) and DIEA (274 μl) were added and stirred at ambient for 15 min. Cis(±)ethyl 4-amino-3-methoxypiperidine-1-carboxylate (Intermediate 21; 317 mg) was added and the mixture was stirred at ambient for 18 h. The mixture was diluted with EtOAc and washed with water, 1N HCl, bicarbonate buffer, water, brine and dried over Na2SO4. The solution was concentrated in vacuo to give the title compound as a brown solid (503 mg). MS (ES) MH+: 378, 380 for C15H21Cl2N3O4; NMR: 1.29 (t, 3H), 1.79 (m, 2H), 2.27 (s, 3H), 3.12 (m, 2H), 3.30 (s, 3H), 3.37 (m, 1H), 3.83-4.16 (m, 5H), 7.25 (d, 1H), 12.23 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399489B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-7feb247f6cce41e79cb12bee4fd27dcf |
| Source note | uspto-grants-2013_03 |