참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Dimethylformamide | HCID 6228 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | cis-2-Fluorocyclopropanecarboxylic acid | HCID 9793716 | — |
| 반응물 | ((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphate | HCID 11038641 | — |
| 반응물 | 7-Bromoisoquinolin-3-amine | HCID 52987757 | — |
| 촉매 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | (1S,2S)-N-(7-bromoisoquinolin-3-yl)-2-fluorocyclopropanecarboxamide | HCID 71115390 | 109.6% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08623889B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_01 |
|---|
| ORD ID | ord-b1f1a2ead6be467e8796a6bb86f36068 |
|---|
| 출처 메모 | uspto-grants-2014_01 |
|---|
