반응 #2161278

반응 방정식

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

용매

MeOH

CH2Cl2

반응 조건

후처리

1. 1
   기타The solvent was removed in vacuo
2. 2
   세척washed with water (2×50 mL), brine (100 mL)
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   기타The resulting gum was azeotroped with EtOAc (2×200 mL)
6. 6
   기타to yield a white solid
7. 7
   온도with heating
8. 8
   workup.WAITleft
9. 9
   기타to crystallize overnight
10. 10
    기타to afford small colorless needles
11. 11
    기타The MeOH was decanted
12. 12
    세척the crystals washed with MeOH (3×15 mL), EtOAc (3×30 mL) and finally hexane (2×25 mL
13. 13
    기타100 mL) and dried at room temperature

실험 절차

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)+.

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