HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylamine → 2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-6-(cyclopropylamino)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | 2-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile | HCID 86643847 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-6-(cyclopropylamino)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile | HCID 68762959 | — |
Reaction Steps
At RT, 50 mg (0.09 mmol) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 0.013 ml (0.19 mmol) of cyclopropanamine were stirred in 1.3 ml of DMF overnight. The crude product was purified directly by preparative HPLC (acetonitrile/water). The collected product fractions were once more dissolved in 2 ml of DMF, 0.013 ml (0.19 mmol) of cyclopropanamine was added and the mixture was stirred at RT overnight. The crude product was then once more purified by preparative HPLC (acetonitrile/water). This gave 20 mg (39% of theory) of the desired target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08420825B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-bf3a802626c64756b9704f9846da48e9 |
| Source note | uspto-grants-2013_04 |