تفاعل #87806

معادلة التفاعل

3-(5-(aminomethyl)-2-chlorophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-5(4H)-one

DMF

TBTU

3-methoxy-2,2-dimethylpropanoic acid

→

desired product

المردود 33.6%

N-(4-Chloro-3-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)-3-methoxy-2,2-dimethylpropanamide

المردود 33.6%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at RT for 2 days
3. 3
   أخرىAfter completion of the reaction
4. 4
   أخرىthe reaction mass was quenched with water
5. 5
   استخلاصextracted with ethyl acetate
6. 6
   أخرىThe organic layer was separated
7. 7
   أخرىdried
8. 8
   تركيزconcentrated
9. 9
   أخرىto obtain crude product
10. 10
    أخرىThe obtained crude
11. 11
    أخرىwas purified with column chromatography on basic alumina
12. 12
    غسيلby eluting with 5.0% MeOH

الإجراء التجريبي

To a solution of 3-(5-(aminomethyl)-2-chlorophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-5(4H)-one (Intermediate-63, 0.250 g, 0.678 mmol) in THF:DMF (5 mL:1 mL), TBTU (0.653 g, 2.3 mmol), TEA (4.0 mL) were added and the reaction mass was stirred at RT for 1 h. To the reaction mixture, 3-methoxy-2,2-dimethylpropanoic acid (0.134 g, 1.01 mmol) was added and stirring was continued at RT for 2 days. After completion of the reaction, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to obtain crude product. The obtained crude was purified with column chromatography on basic alumina by eluting with 5.0% MeOH:DCM to afford 0.110 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 1.15 (s, 6H), 1.18 (s, 3H), 3.09 (t, 2H), 4.32 (d, J=11.4 Hz, 2H), 7.43 (dd, J=4.5 Hz, 3.6 Hz, 1H), 7.45 (d, 1H), 7.86 (d, J=5.4 Hz, 2H), 8.15 (t, 1H), 8.20 (d, 2H), 12.50 (br s, 1H); MS (m/z): 483.20 (M+H)+.

المصدر