Reaktion #45052

Reaktionsgleichung

NH4Cl

NaHMDS

methyl 4-(4-methylpiperazine-1-carbonyl)benzoate

tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]-1H-pyrazole-1-carboxylate

→

title compound

Ausbeute 56.6%

N-[5-[2-(3,5-Dimethoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-(4-methylpiperazine-1-carbonyl)benzamide

Ausbeute 56.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (2×25 mL)
2. 2
   Waschenwashed with saturated brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto afford the crude product (0.501 g) as a yellow gum
7. 7
   SonstigeThe crude product was purified by preparative HPLC
8. 8
   workup.ADDITIONFractions containing the desired compound
9. 9
   Sonstigewere evaporated to dryness

Vorschrift

A solution of NaHMDS (1M in THF) (2.86 mL, 2.86 mmol) was added dropwise to a stirred solution of methyl 4-(4-methylpiperazine-1-carbonyl)benzoate (0.250 g, 0.95 mmol) and tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]-1H-pyrazole-1-carboxylate (0.397 g, 1.14 mmol) in THF (2 mL), over a period of 10 mins under nitrogen. The resulting solution was stirred at room temperature for 18 h. The reaction mixture was poured into saturated NH4Cl (25 mL), extracted with EtOAc (2×25 mL), washed with saturated brine and dried over MgSO4, filtered and evaporated to afford the crude product (0.501 g) as a yellow gum. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% ammonium hydroxide) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.257 g, 56.5%) as a yellow solid; 1H NMR (399.9 MHz, DMSO-d6) δ 2.21 (3H, s), 2.25-2.40 (4H, m), 2.89 (4H, s), 3.16-3.20 (1H, d), 3.32 (4H, s), 3.72 (6H, d), 6.33 (1H, m), 6.42-6.44 (2H, d), 7.46-7.50 (2H, d), 8.02-8.06 (2H, d)

Quelle