HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
6-Bromopyridine-2-carboxylic acid → 3-Amino-1-(4-(cyclohexylmethoxy)pyridin-2-yl)propan-1-ol
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 6-Bromopyridine-2-carboxylic acid | HCID 593919 | — |
| Edukt | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Edukt | Ammonia methanol dichloromethane | HCID 21584172 | — |
| Edukt | 3-(4-(Cyclohexylmethoxy)pyridin-2-yl)-3-oxopropanenitrile | HCID 86694597 | — |
| Produkt | 3-Amino-1-(4-(cyclohexylmethoxy)pyridin-2-yl)propan-1-ol | HCID 86694596 | — |
Reaktionsschritte
Reduction of 3-(4-(cyclohexylmethoxy)pyridin-2-yl)-3-oxopropanenitrile with borane-dimethylsulfide following the method used in Example 2 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 12 as a yellow oil. Yield (0.13 g, 43%); 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J=4.5 Hz, 1H), 6.98 (d, J=2.3 Hz, 1H), 6.76 (dd, J=5.9, 2.8 Hz, 1H), 4.62-4.58 (m, 1H), 3.94 (d, J=5.8 Hz, 2H), 2.72-2.58 (m, 2H), 1.88-1.58 (m, 8H), 1.40-1.02 (m, 5H); RP-HPLC tR=5.91 min; ESI-MS m/z 265.2 [M+H]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09447078B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-d364b0c9c76740a195264120bee4dcfa |
| Quellennotiz | uspto-grants-2016_09 |