تفاعل #68601

معادلة التفاعل

sodium hydrosulfide

tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

hydroxylamine-O-sulfonic acid

sodium bicarbonate

→

tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

المردود 22.5%

المذيبات

water

water

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature overnight
2. 2
   استخلاصextracted with DCM (40 mL)
3. 3
   تجفيفdried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   تركيزThe concentrated crude material
7. 7
   workup.DISSOLUTIONwas dissolved in minimal DCM
8. 8
   أخرىwas purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM)

الإجراء التجريبي

An aqueous mixture of tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.800 g, 2.33 mmol) and hydroxylamine-O-sulfonic acid (0.263 g, 2.33 mol) in water (8.0 mL) and 1,4-dioxane (8.0 mL) was stirred at 0° C. until complete consumption of the organic starting material was observed. The mixture was then carefully treated with solid sodium bicarbonate (0.196 g, 2.33 mmol), followed by treatment with 1.4 M aqueous sodium hydrosulfide (1.83 ml, 2.56 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with DCM (40 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The concentrated crude material was dissolved in minimal DCM and was purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM) to yield tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.196 g, 22.5% yield) with 82% purity. MS (ESI pos. ion) m/z: 433.0 (M+H). Calc'd Exact Mass for C21H20N8OS: 432.51.

المصدر