Ethyl 4-(piperazin-1-yl)benzoate → N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide

HRID 1092058노트

반응식

HRID 1092058 반응식
C[Al](C)C.[C:5]([N:9]1[C:13]([NH2:14])=[CH:12][C:11]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[N:10]1)([CH3:8])([CH3:7])[CH3:6].[N:25]1([C:31]2[CH:41]=[CH:40][C:34]([C:35](OCC)=[O:36])=[CH:33][CH:32]=2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[C:5]([N:9]1[C:13]([NH:14][C:35](=[O:36])[C:34]2[CH:33]=[CH:32][C:31]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:41][CH:40]=2)=[CH:12][C:11]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[N:10]1)([CH3:8])([CH3:7])[CH3:6]

참가 물질

5

반응물 3

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 16682925TrimethylaluminumHCID 574539341-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine

생성물 1

HCID 66589920N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide수율 22.53%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
20 °C

실험 절차

A 2M solution of trimethylaluminium in toluene (6.25 mL, 12.50 mmol) was added dropwise to a stirred solution of and 1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine (1.367 g, 5.00 mmol) and ethyl 4-(piperazin-1-yl)benzoate (1.171 g, 5 mmol) in toluene (20 mL) at 4° C., over a period of 5 mins under nitrogen. The resulting solution was stirred at 20° C. for 18 h. The reaction mixture was quenched with methanol (20 mL), filtered and evaporated to afford tan solid. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM and 0.1% ammonia. Pure fractions were evaporated to dryness to afford N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide (0.520 g, 22.53%) as a white solid.

후처리

  1. customThe reaction mixture was quenched with methanol (20 mL)
  2. filtrationfiltered
  3. customevaporated
  4. customto afford tan solid
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 10% MeOH in DCM and 0.1% ammonia
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-120e15959afe4ff7ba6c9e78650543aa
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129391B2

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