乙炔胺

实验步骤: 投料: 取25ml干燥双口瓶，加入2-(pyren-1-yl)aniline（100mg 340.87umol 1eq）和5ml乙腈，在缓慢滴加亚硝酸叔丁酯(52.73mg 511.30umol 1.5eq)。反应液室温搅拌下反应5h。

实验步骤: 投料: 取25ml干燥双口瓶，加入2-(pyren-1-yl)aniline（100mg 340.87umol 1eq）和5ml乙腈，在缓慢滴加亚硝酸叔丁酯(52.73mg 511.30umol 1.5eq)。反应液室温搅拌下反应5h。\n监测: 取反应液TLC点板和lcms监测，原料剩余，故继续反应。\n监测: 取反应液点板和lcms监测，原料剩余不多。\n后处理: 点板监测，原料反应完全，故停止反应。减压浓缩除去溶剂乙腈，加入30mL乙酸乙酯和20mL水萃取，分液，水相用20mL乙酸乙酯反萃两次，合并上述有机相。有机相用饱和食盐水洗涤，无水硫酸钠干燥，过滤，有机相滤液减压浓缩干，得到粗品。\n刮大板确定结构: 将粗品爬大板，展开剂为PE，刮下疑似产物带，送核磁监测。\n送核磁监测: 将疑似产物带刮下，用EA浸泡硅胶，过滤真空浓缩，得到荧光黄固体，加入0.5ml氘代DMSO，送核磁监测。

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]acetic acid (80.0 mg, 0.184 mmol) and acetylenamine (11.68 mg, 0.190) in anhydrous DMF (1 mL) was added HOBt (28.2 mg, 0.184 mmol) followed by EDC (70.7 mg, 0.368 mmol) and the mixture was stirred at room temperature under nitrogen atmosphere for 16 hours. The mixture was diluted with water and ethyl acetate (5 mL). The layers were separated, the aqueous phase extracted with EtOAc (5 ml), the organic fractions combined, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via preparative TLC plate (1000 μM) using 40% ethyl acetate in hexane. The band containing product was removed from the plate and the silica washed with EtOAc. The filtrate was collected and the volatiles removed in vacuo to afford the title compound. HPLC/MS; 1.49 min (2 minute run), 471 (M+H)+. The layers were separated the aqueous phase extracted with EtOAc (5 ml) dried over sodium sulfate filtered concentrated in vacuo The residue was purified via preparative TLC plate (1000 μM) The band containing product was removed from the plate the silica washed with EtOAc The filtrate was collected the volatiles removed in vacuo