تفاعل #2161278

معادلة التفاعل

sulfonyl chloride

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine

triethylamine

→

title compound

N-(1-{2-[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)methanesulfonamide

المذيبات

MeOH

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed in vacuo
2. 2
   غسيلwashed with water (2×50 mL), brine (100 mL)
3. 3
   تجفيفdried over MgSO4
4. 4
   ترشيحfiltered
5. 5
   أخرىThe resulting gum was azeotroped with EtOAc (2×200 mL)
6. 6
   أخرىto yield a white solid
7. 7
   درجة الحرارةwith heating
8. 8
   workup.WAITleft
9. 9
   أخرىto crystallize overnight
10. 10
    أخرىto afford small colorless needles
11. 11
    أخرىThe MeOH was decanted
12. 12
    غسيلthe crystals washed with MeOH (3×15 mL), EtOAc (3×30 mL) and finally hexane (2×25 mL
13. 13
    أخرى100 mL) and dried at room temperature

الإجراء التجريبي

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (1.13 g, 2.87 mmol) in CH2Cl2 (10 mL) was added triethylamine (442.0 μL, 3.20 mmol) followed by sulfonyl chloride (223.0 μL, 2.87 mmol) and the reaction stirred at 25° C. for 1 hour. The solvent was removed in vacuo, and the residue was taken up in EtOAc (200 mL) and washed with water (2×50 mL), brine (100 mL), dried over MgSO4, filtered and stripped. The resulting gum was azeotroped with EtOAc (2×200 mL) to yield a white solid. The white solid was taken up in MeOH (25 mL) with heating, and left to crystallize overnight to afford small colorless needles. The MeOH was decanted and the crystals washed with MeOH (3×15 mL), EtOAc (3×30 mL) and finally hexane (2×25 mL, then 100 mL) and dried at room temperature to yield the title compound as white needles, 968 mg, 72 %. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.53 (d, 2 H), 7.65 (d, 2 H), 7.30 (t, 2 H), 7.20 (s, 1 H), 7.15 (t, 2 H), 6.52 (s, 1 H), 5.18 (q, 2 H), 4.10 (d, 1 H), 3.93 (s, 2 H), 3.83 (d, 1 H), 3.36-3.46 (m, 1 H), 3.17 (t, 1 H), 2.94 (s, 3 H), 2.80 (t, 1 H), 1.79-1.92 (m, 2 H), 1.41-1.52 (m, 1 H), 1.23-1.34 (m, 1 H); m/z (APCI+) for C23H26N5O3FS 472.1 (M+H)+.

المصدر