HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-1H-inden-2-ylmethyl)acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-Methyl-2-(methylaminomethyl)indene hydrochloride | HCID 22138219 | — |
| Reactant | 3-(2-Amino-3-pyridyl)acrylic acid | HCID 22593811 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-3-[6-aminopyridin-3-yl]-N-methyl-N-(3-methyl-1H-inden-2-ylmethyl)acrylamide | HCID 22593796 | 52% |
Reaction Steps
EDC (0.383 g, 2.0 mmole) was added to a solution of (E)-3-(o-aminopyridin-3-yl)acrylic acid (0.328 g, 2.0 mmole), 3-methyl-2-(methylaminomethyl)indene hydrochloride (0.420 g, 2.0 mmole), HOBt.H2O (0.306 g, 2.0 mmole), and triethylamine (0.57 mL, 4.0 mmole) in anhydrous DMF (18 mL) at RT. The reaction was stirred overnight and concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (0.33 g, 52%) as a colorless solid: MS (ES) m/e 320.2 (M+H)+. Anal. Calcd for C20H21N3O. 0.4 H2O; C, 73.57; H, 6.72; N, 12.86. Found: C, 73.94; H, 6.92; N, 12.50.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173646B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-b68b7db77a0f4b28805bf38f9e839f2e |
| Source note | uspto-grants-2012_05 |