4-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → Piperidine-4-carboxylic acid [6-(2-benzyloxy-phenyl)-pyrimidin-4-yl]-amide
반응식
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:39])[NH:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>Br.C(O)(=O)C>[CH2:32]([O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:22]=[CH:21][N:20]=[C:19]([NH:18][C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[O:39])[CH:24]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1참가 물질
4
실험 절차
4-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XVI) (0.5 g, 1 mmol) was dissolved in 33% HBr in acetic acid (3 ml) and stirred at room temperature for 45 minutes. A yellow solid precipitated out; the reaction mixture was quenched at 0° C. with aqueous sodium hydroxide solution and extracted with ethyl acetate (3×10 ml). The organic phases were separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by preparative HPLC (C-18, AcN:H2O with 0.05% TFA) and lyophilized to afford piperidine-4-carboxylic acid [6-(2-benzyloxy-phenyl)-pyrimidin-4-yl]-amide (compound #9A) (0.028 g, 7%) as a white solid.