Dimethylformamide → Morpholine-4-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

温度

50 °C

To a solution of 2-phenylacetyl chloride (0.0523 ml) in acetonitrile (5.0 ml) was added potassium thiocyanate (35.6 mg), followed by stirring under a nitrogen atmosphere at 50° C. for 1 hr. The reaction mixture was cooled down to room temperature, and then morpholine-4-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridine-2-yl]amide (80 mg) and N,N-dimethylformamide (1 ml) were added thereto, followed by stirring under a nitrogen atmosphere at room temperature for 21 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a solid, which was suspended in diethyl ether (4 ml)-ethanol (0.8 ml). The solid was filtered off, washed with diethyl ether, and dried under aeration to provide the titled compound (38 mg, 31%) as colorless powder.

1. temperatureThe reaction mixture was cooled down to room temperature
2. stirringby stirring under a nitrogen atmosphere at room temperature for 21 hrs
3. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml)
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated
7. customto give a residue, which
8. customwas then purified by silica gel column chromatography (eluent; ethyl acetate)
9. additionFractions containing the target compound
10. concentrationwere concentrated
11. customto give a solid, which
12. filtrationThe solid was filtered off
13. washwashed with diethyl ether
14. customdried under aeration

ORDレコード

ord-b2dcf3806dde4311904453cc29d95adc

出典データセット

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07531532B2