HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-amino-3-ethoxy-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide
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-Amino-3-ethoxybenzoic acid | HCID 22397448 | — |
| Reactant | (3R)-1-Methyl-3-PyrrolidinaMine hydrochloride | HCID 53256048 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-amino-3-ethoxy-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide | HCID 68681219 | 68% |
Reaction Steps
4-amino-3-ethoxybenzoic acid (Intermediate 164; 400 mg, 2.21 mmol), HATU (1.26 g, 3.31 mmol) and (3R)-1-methylpyrrolidin-3-amine di Hydrochloride (Intermediate 184; 453 mg, 3.31 mmol) were stirred in DMF (5 mL) and diisopropylethylamine (1.7 ml, 9.95 mmol) added. The mixture was stirred for 2 hours and then absorbed on to an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and purified by column chromatography (2.5% ammonia in methanol/DCM) to yield the title compound as a yellow foam (396 mg, 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709471B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-55e2f798c47a411fa4181be1cec3b864 |
| Source note | uspto-grants-2010_05 |