関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | cis-2-Fluorocyclopropanecarboxylic acid | HCID 9793716 | — |
| 反応物 | ((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphate | HCID 11038641 | — |
| 反応物 | 7-Bromoisoquinolin-3-amine | HCID 52987757 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (1S,2S)-N-(7-bromoisoquinolin-3-yl)-2-fluorocyclopropanecarboxamide | HCID 71115390 | 109.6% |
反応手順
A mixture of 7-bromoisoquinolin-3-amine (4.531 g, 20.31 mmol), (1S,2S)-2-fluorocyclopropanecarboxylic acid (2.002 g, 19.24 mmol), (7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (12.148 g, 23.433 mmol), N,N-diisopropylethylamine (8.50 mL, 48.8 mmol), 4-dimethylaminopyridine (0.245 g, 2.00 mmol), and N,N-dimethylformamide (100 mL, 1000 mmol) was stirred at 50° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude residue was purified via flash chromatography on silica gel (120 g silica, solvent gradient: 0-30% ethyl acetate in dichloromethane) to yield 6.5208 g of the title compound. LCMS (ESI): M+H=309.2.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08623889B2 |
|---|
| 出典データセット | uspto-grants-2014_01 |
|---|
| ORD ID | ord-b1f1a2ead6be467e8796a6bb86f36068 |
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| 出典メモ | uspto-grants-2014_01 |
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