Dimethylformamide → HCID 178487445、化合物

反応式

Br[C:2]1[N:3]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH:32]3CC3)=[CH:24][CH:23]=2)[C:4]([S:7]CC(NC2C=CC(C(O)=O)=CC=2Cl)=O)=[N:5][N:6]=1.Cl.NNC(N)=N.C([N:44](C(C)C)CC)(C)C.CN(C)[CH:52]=[O:53]>>[NH2:44][C:2]1[N:3]([C:22]2[C:27]3[C:26](=[CH:31][CH:30]=[C:29]([O:53][CH3:52])[CH:28]=3)[C:25]([CH3:32])=[CH:24][CH:23]=2)[C:4]([SH:7])=[N:5][N:6]=1

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 16221816Rdea806

HCID 178418668HCID 178418668、化合物

生成物 1

HCID 178487445HCID 178487445、化合物収率 91%

反応条件

温度: 50 °C

実験手順

Compound 6 (826 mg, 4.4 mmol) was dissolved in 25 mL of dichloromethane. Sodium bicarbonate (15 mL, sat. solution) and thiophosgene (0.34 mL, 4.4 mmol) were added and the mixture stirred at room temperature for 1 h. Then, the organic layer was separated, dried over sodium sulfate and concentrated to afford 1.9 g, 99% yield of 4-isothiocyanato-6-methoxy-1-methylnaphthalene (7) which was used in the next step without further purification Compound 7 (1.0 g, 4.4 mmol) was dissolved in 10 mL of dimethylformamide, aminoguanidine hydrochloride salt (723 mg, 6.5 mmol) and diisopropyl ethylamine (1.14 mL, 6.5 mmol) were added and the mixture stirred at 50° C. for 18 hours. The mixture was then concentrated and to the resulting residue was added 2M aqueous sodium hydroxide solution (10 mL). The mixture was stirred at 50° C. for 18 hours and then cooled to room temperature. The resulting mixture was then neutralized with aqueous 1N HCl and the precipitate (product) collected to give 5-amino-4-(7-methoxy-4-methylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (8). (1.14 mg, 91% yield)