反応 #90769

反応方程式

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

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

cesium carbonate

BINAP

→

title compound

収率 16.1%

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

収率 16.1%

反応条件

後処理

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

実験手順

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).

出典