Реакция #45052

Уравнение реакции

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

Выход 56.6%

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

Выход 56.6%

Растворители

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with EtOAc (2×25 mL)
2. 2
   Промывкаwashed with saturated brine
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated
6. 6
   Другоеto afford the crude product (0.501 g) as a yellow gum
7. 7
   ДругоеThe crude product was purified by preparative HPLC
8. 8
   workup.ADDITIONFractions containing the desired compound
9. 9
   Другоеwere evaporated to dryness

Методика

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)

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