Methyl iodide → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-methoxy-5-trifluoromethyl-phenyl)-2-methyl-isothiourea

온도

0 °C

(Reaction performed under N2 atmosphere) NaH (1.267 g, 0.05279 mol) was added portionwise to an ice-cooled solution of intermediate D5 (21.32 g, 0.05279 mol) in THF (480 ml) and the resulting mixture was stirred for 15 minutes at 0° C. Subsequently, a solution of CH3I (7.493 g, 0.05279 mol) in THF (40 ml) was added dropwise and the mixture was stirred for 2 hours at room temperature. Then the reaction mixture was quenched with H2O and extracted with CH2Cl2 (3×500 ml). The organic layers were separated, combined, washed with brine, dried (MgSO4), filtered and the solvent was evaporated in vacuo. The crude product was triturated with DIPE/heptane. The off-white solid was filtered off and dried to yield 16.203 g of intermediate D6 (73.5%). Heptane and H2O were added to the filtrate and this mixture was stirred overnight at room temperature. The off-white precipitate was filtered off and dried to yield more (1.957 g) of intermediate D6 (9%).

1. stirringthe mixture was stirred for 2 hours at room temperature
2. customThen the reaction mixture was quenched with H2O
3. extractionextracted with CH2Cl2 (3×500 ml)
4. customThe organic layers were separated
5. washwashed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customthe solvent was evaporated in vacuo
9. customThe crude product was triturated with DIPE/heptane
10. filtrationThe off-white solid was filtered off
11. customdried

ORD 기록

ord-ce136f6928c54b8fa7c8c18644ecfcc0

출처 데이터셋

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08440701B2