HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,2-Dichloroethane → (E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indazol-3-ylmethyl)acrylamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,2-Dichloroethane | HCID 11 | — |
| Edukt | Water | HCID 962 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | N-Methyl-N-[(1-methyl-1H-indazol-3-yl)methyl]amine | HCID 7537473 | — |
| Edukt | (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid | HCID 10487224 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | (E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indazol-3-ylmethyl)acrylamide | HCID 9797187 | 74,1% |
Reaktionsschritte
EDC (230 mg, 1.2 mmole) was added to a solution (E)3-(6-aminopyridin-3-yl)acrylic acid (164 mg, 1.0 mmole), 1-methyl-3-(methylaminomethyl)-1H-indazole (210 mg, 1.2 mmole), HOBt.H2O (162 mg, 1.2 mmole), and Et3N (0.28 mL, 2.0 mmole) in dry DMF (5 mL) at RT. After 18 hr the mixture was concentrated. Flash chromatography on silica gel (5% EtOH/EtOAc) gave the title compound (238 mg, 74%) as a white foam: 1H NMR (400 MHz, CDCl3) δ 8.24 (m, 1 H), 7.90 (m, 1 H), 7.65 (m, 2 H), 7.35 (m, 2 H), 7.09 (m, 1 H), 6.73 (m, 1 H), 6.50 (m, 1 H), 5.04 (s, 2 H), 4.83 (bs, 2 H), 4.04 (s, 3 H), 3.10 (s, 3 H); MS (ES) m/e 322 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07557125B2 |
| Quelldatensatz | uspto-grants-2009_07 |
| ORD ID | ord-61e84506eff941b28091198715f827c1 |
| Quellennotiz | uspto-grants-2009_07 |