Bromotrimethylsilane → [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2ylsulfanylmethyl]-phosphonic acid

To a solution of [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2-ylsulfanylmethyl]-phosphonic acid diethyl ester 12-1 (140 mg, 0.29 mmol) in CH2Cl2 (0.8 mL) and hexamethyldisilazane (0.8 mL) was added bromotrimethylsilane (0.40 mL, 3.0 mmol). After stirring overnight at room temperature, the volatiles were removed from the mixture via a rotary evaporator. The resulting residue was dissolved in EtOAc (2 mL) and filtered through a 0.45 μm syringe filter. The filtrate was evaporated to dryness, and anhydrous MeOH was added. The mixture was triturated by sonication from MeOH to give a suspension of a fine white solid. The solid was isolated by centrifugation followed by decanting the MeOH. The resulting solid was furthered purified by a second trituration in MeOH, and then dried under vacuum at 40° C. overnight to afford the title compound 12-2. LRMS (API-ES) m/e for C15H13Cl2N2O3PS (M+H)+, calcd 403.23. found 403.1. Anal. Calcd for C15H13Cl2N2O3PS: C, 44.68; H, 3.25; N, 6.95. Found: C, 44.44; 1-1, 3.43; N, 6.68.

1. customthe volatiles were removed from the mixture via a rotary evaporator
2. dissolutionThe resulting residue was dissolved in EtOAc (2 mL)
3. filtrationfiltered through a 0.45 μm syringe
4. filtrationfilter
5. customThe filtrate was evaporated to dryness, and anhydrous MeOH
6. additionwas added
7. customThe mixture was triturated by sonication from MeOH
8. customto give
9. additiona suspension of a fine white solid
10. customThe solid was isolated by centrifugation
11. customby decanting the MeOH
12. customThe resulting solid was furthered purified by a second trituration in MeOH
13. customdried under vacuum at 40° C. overnight

ORDレコード

ord-8a33a54f42674f2d8570eb2121158dce

出典データセット

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08329914B2