反応 #59095

反応方程式

3-(tert-Butyl)benzenisothiocyanate

N-{4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-2-(4-methylpiperidyl)acetamide

Thiourea

→

N-[4({2-[(3-tert-butylphenyl)amino]-1-methyl-1-H-benzimidazol-5-yl}oxy)pyridin-2-yl]-2-(4-methylpiperidin-1-yl)acetamide

溶媒

methanol

反応条件

後処理

1. 1
   その他Reaction
2. 2
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 4 hours
3. 3
   濃縮was concentrated
4. 4
   workup.ADDITIONaqueous sodium carbonate was added until basic pH
5. 5
   その他The reaction mixture was partitioned between ethyl acetate and water
6. 6
   洗浄The organic layer was washed with water
7. 7
   乾燥brine, and dried over sodium sulfate
8. 8
   濃縮concentrated
9. 9
   その他The crude product was purified by reverse phase HPLC

実験手順

3-(tert-Butyl)benzenisothiocyanate was added to a solution of N-{4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-2-(4-methylpiperidyl)acetamide in methanol. Reaction was stirred at room temperature for 15 hours. Thiourea formation was confirmed by LC/MS. Ferric chloride was added and the resulting mixture was stirred at room temperature for 4 hours. After cyclization was complete by LC/MS the reaction mixture was concentrated and aqueous sodium carbonate was added until basic pH. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water then brine, and dried over sodium sulfate and concentrated. The crude product was purified by reverse phase HPLC. MS: MH+=527.2.

出典