3-Pyridinylboronic acid → 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide
반응식
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:26])[C:15]=3[N:14]=[C:13]2[CH2:27][O:28][CH2:29][CH3:30])=[CH:5][CH:4]=1.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39](B(O)O)[CH:38]=1>>[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20]([C:39]5[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=5)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:26])[C:15]=3[N:14]=[C:13]2[CH2:27][O:28][CH2:29][CH3:30])=[CH:5][CH:4]=1참가 물질
3
실험 절차
4-Methoxybenzyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (1.16 g, 2.0 mmol) and pyridine-3-boronic acid (0.30 g, 2.4 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, at which time additional pyridine-3-boronic acid (0.3 equivalent) was added and the reaction was heated for an additional five hours. The work-up procedure used in Part F of Examples 125–135 was followed. The crude product was purified by column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 100:0 to 80:20) and then triturated with methanol, isolated by filtration, and dried for 20 hours under high vacuum at 140° C. to provide 0.62 g of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as a beige powder, mp 230–231.5° C.