Trifluoroacetic acid → HCID 178488911、化合物

反応式

COC1C=CC(C[N:8]2[C:12]3[N:13]=[C:14]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:15]4[C:16](=[O:31])[NH:17][C:18]5[CH:24]=[C:23]([N:25]6[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]6)[CH:22]=[CH:21][C:19]=5[C:20]=4[C:11]=3[C:10]([CH3:40])=[N:9]2)=CC=1.C(OC(C)C)(C)C.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([C:14]2[C:15]3[C:16](=[O:31])[NH:17][C:18]4[CH:24]=[C:23]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:22]=[CH:21][C:19]=4[C:20]=3[C:11]3[C:10]([CH3:40])=[N:9][NH:8][C:12]=3[N:13]=2)=[CH:33][CH:34]=1

参加物

反応物 3

HCID 6422Trifluoroacetic acid

HCID 7914Diisopropyl Ether

HCID 136642863HCID 136642863、化合物

生成物 1

HCID 178488911HCID 178488911、化合物

実験手順

A solution of 4.5 g (8.03 mmol) of 3-(4-methoxybenzyl)-5-(4-methoxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one dissolved in 70 ml of trifluoroacetic acid is carried at 70° C. for 4 hours and then cooled to room temperature before the addition of isopropyl ether (150 ml). The reaction medium is stirred at room temperature for 30 minutes and then the precipitate obtained is filtered to yield 5-(4-methoxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one trifluoroacetate. The solid is dissolved in 180 ml of anhydrous dichloroethane. The reaction medium is cooled to 0° C. before the slow addition of 43.3 ml (43.3 mmol) of a 1 M solution of boron tribromide in dichloromethane. The reaction medium is carried at reflux for 7 hours and then cooled again to 0° C. Methanol (approximately 200 ml) is added and then the reaction medium is stirred for 2 hours. The solid obtained is filtered and then triturated several times in hot methanol. A final filtration yields 2.6 g (47%) of 5-(4-hydroxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one hydrobromide in the form of an orange solid.