반응 #90769

반응 방정식

2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide

3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine

cesium carbonate

BINAP

→

title compound

수율 16.1%

2-[(5-Chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide

수율 16.1%

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed with nitrogen for 10 min
2. 2
   기타The crude material was purified on reverse-phase HPLC (Gilson)
3. 3
   세척eluting with CH3CN/H2O with 0.1% formic acid which

실험 절차

A microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (70 mg, 0.224 mmol), {3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (70 mg, 0.503 mmol) and cesium carbonate (230 mg, 0.706 mmol). The reaction mixture was degassed with nitrogen for 10 min. At same time, BINAP (50 mg, 0.080 mmol) and palladium(II) acetate (10 mg, 0.045 mmol) were added. The reaction mixture was heated in a microwave at 160° C. for 40 min. The crude material was purified on reverse-phase HPLC (Gilson) eluting with CH3CN/H2O with 0.1% formic acid which gave a title compound (15 mg, 15%); MS: M(C20H23ClN6O2)=414.89, (M+H)+=415, 416; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.42 (br. s., 1 H) 8.71 (br. s., 1 H) 8.02 (s, 1 H) 7.54 (br. s., 1 H) 7.06 (t, J=7.5 Hz, 1 H) 6.48 (s, 1 H) 6.32 (br. s., 1 H) 5.86 (s, 1 H) 4.47 (dt, J=13.4, 6.7 Hz, 1 H) 3.92 (s, 3 H) 2.26 (s, 3 H) 1.41-1.43 (d, J=6.6 Hz, 2 H).

출처