HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-Amino-4-methylthiazole → 3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2-Amino-4-methylthiazole | HCID 74143 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Edukt | 3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid | HCID 66971931 | — |
| Edukt | 3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxo pyrrolidin-3-yloxy)benzoic acid | HCID 66972226 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide | HCID 50914585 | — |
Reaktionsschritte
4-(Dimethylamino)pyridine (DMAP) (0.149 g), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI.HCl) (0.524 g) were added to a solution of 3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid (0.5 g) (Intermediate 1) in dry DCM under nitrogen at 0-5° C. 2-amino-4-methyl thiazole (0.134 g) was added and the mixture was stirred for 16 h at room temperature. It was diluted with commercially available DCM. Organic phase was washed with dil HCl, saturated solution of NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated in vacuo to get the crude residue. The residue was chromatographed to yield pure titled compound (0.3 g) as a white solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08835469B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-c3472dd1329b4842b0869dd491a8adc9 |
| Quellennotiz | uspto-grants-2014_09 |