Acetyl chloride → HCID 21999034、化合物

反応式

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[C:4]([C:12]2[C:13](=[O:29])[NH:14][C:15](=[O:28])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][C:22]([NH2:26])=[CH:23][CH:24]=3)[N:19]([CH3:27])[CH:18]=2)=[CH:3]1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].[O:41]1CC[CH2:43][CH2:42]1>>[C:37]([NH:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([C:16]3[C:15](=[O:28])[NH:14][C:13](=[O:29])[C:12]=3[C:4]3[C:5]4[C:10](=[CH:9][C:8]([NH:11][C:42](=[O:41])[CH3:43])=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:18][N:19]2[CH3:27])=[CH:24][CH:23]=1)(=[O:39])[CH3:38]

参加物

反応物 4

HCID 6367Acetyl chloride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 21999014HCID 21999014、化合物

生成物 1

HCID 21999034HCID 21999034、化合物収率 23%

反応条件

温度: 0 °C

実験手順

3,4-Bis-(1-methyl-6-amino-1H-indol-3-yl)-pyrrole-2,5-dione (50 mg, 0.13 mmole) was dissolved in tetrahydrofuran (2.5 mL) and cooled to 0° C. Triethylamine (38.5 μl, 0.27 mm) was added followed by acetyl chloride (19.4 pl, 0.27 mmole). The reaction was stirred for 30 min, then concentrated. The reaction mixture was dissolved in chloroform, washed with 0.1 N hydrochloric acid and the organic was dried over magnesiun sulfate, filtered and concentrated. The product was purified by column chromatography in 5% methanol/ethyl acetate to give N-{3-[4-(6-acetylamino-1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1-methyl-1H-indol-6-yl}-acetamide (14 mg, 23%).