Ethanol → HCID 178465760、化合物

反応式

[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:26])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:27][O:28][C:29]([NH:31][C:32](=NC(OC)=O)SC)=[O:30].[CH2:40](O)[CH3:41]>>[CH3:27][O:28][C:29](=[O:30])[NH:31][C:32]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3([O:26][CH2:40][CH3:41])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:18])[N:10]3[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:3][C:2]=2[N:1]=1

参加物

反応物 3

HCID 702Ethanol

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate

HCID 67044654HCID 67044654、化合物

生成物 1

HCID 178465760HCID 178465760、化合物

実験手順

A solution of 3-(3,4-diaminophenyl)-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (1.5 g, 4.34 mmol) and 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.8 g, 8.68 mmol) in anhydrous ethanol (15 mL) was heated to 95° C. and stirred for 18 h, at which time the reaction mixture was cooled to room temperature. The white precipitate was filtered and the powder was triturated in hot ethanol (50 mL). The white powder was collected by filtration to afford methyl{5-[1-(ethyloxy)-3-oxo-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-yl]-1H-benzimidazol-2-yl}carbamate (700 mg). 1H NMR (400 MHz, d6-DMSO): 7.82-7.81 (m, 1H), 7.58-7.52 (m, 3H), 7.51 (d, 1H), 7.33-7.16 (m, 6H), 6.90 (d, 1H), 4.75 (d, 1H), 4.75 (d, 1H), 3.79 (d, 1H), 2.74-2.67 (m, 2H), 0.65 (t, 3H); 13C NMR (100 MHz, d6-DMSO): 166.9, 154.5, 147.8, 145.7, 137.6, 132.6, 131.1, 130.7, 130.6, 129.4, 128.3, 127.8, 126.8, 122.9, 122.8, 118.9, 95.3, 57.9, 52.4, 42.5, 14.1; MS (EI) for C26H24N4O4: 457 (MH+).