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Dimethylformamide → 4-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Thionyl Chloride | HCID 24386 | — |
| 反応物 | 6-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one | HCID 135471553 | — |
| 生成物 | 4-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline | HCID 11002191 | 76% |
反応手順
A solution of 6-methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one (1.5 g, 4.7 mmol) in thionyl chloride (15 ml) containing DMF (1.5 ml) was heated at reflux for 3 hours. After cooling, the volatiles were removed under vacuum. The residue was azeotroped with toluene. The solid was partitioned between methylene chloride and sodium hydrogen carbonate. The aqueous layer was adjusted to pH10 with 6M aqueous sodium hydroxide. The organic layer was separated, washed with brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography to give 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (1.21 g, 76%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08492560B2 |
| 出典データセット | uspto-grants-2013_07 |
| ORD ID | ord-f166a99e3e2c40ca95a00b88db32b65a |
| 出典メモ | uspto-grants-2013_07 |