تفاعل #78464

معادلة التفاعل

ethyl acetate

4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)amino]-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one

hydrochloric acid

potassium carbonate

→

title compound

المردود 91.4%

(+)-6-[Amino-(6-Chloro-Pyridin-3-yl)-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-4-(3-Chloro-Phenyl)-1-Cyclopropylmethyl-1H-Quinolin-2-One

المردود 91.4%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled to 0° C
2. 2
   أخرىAfter separation
3. 3
   غسيلthe organic layer was washed with brine
4. 4
   تجفيفdried over MgSO4
5. 5
   تركيزconcentrated under vacuum
6. 6
   أخرىto give the crude product
7. 7
   أخرىIt was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 2:98:0.1) as the eluents

الإجراء التجريبي

To a solution of the title compound of Example 45, the slower moving enantiomer of 4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)amino]-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one (1.41 g, 1.74 mmol) in THF (200 ml) was added 2N hydrochloric acid (20 ml) slowly. The reaction mixture was stirred at ambient temperature for 1.5 hour after which time it was cooled to 0° C. An aqueous solution of potassium carbonate was added followed by addition of ethyl acetate. After separation, the organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 2:98:0.1) as the eluents to afford the title compound as a white solid ( 0.844 g, 1.59 mmol, 90% yield). It is the faster eluting enantiomer of 6-[amino-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one with >99% optical purity.

المصدر