1,1'-Carbonyldiimidazole → 1-(3-Cyclopropylpropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}urea

HRID 2424512노트

반응식

HRID 2424512 반응식
[NH2:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:26]([N:33]1[CH:37]=[CH:36]N=C1)(N1C=CN=C1)=[O:27].[CH:38]1([CH2:41]CCN)[CH2:40][CH2:39]1>ClCCl>[CH:38]1([CH2:41][CH2:36][CH2:37][NH:33][C:26]([NH:1][C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]3)=[CH:4][CH:3]=2)=[O:27])[CH2:40][CH2:39]1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 204265043-Cyclopropylpropan-1-amine HydrochlorideHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

생성물 1

HCID 112368931-(3-Cyclopropylpropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}urea수율 8.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone (200 mg, 0.57 mmol) was slowly added to an ice cold solution of 1,1′-carbonyldiimidazole (110 mg, 0.683 mmol) in anhydrous dichloromethane (15 mL). The temperature was then raised to ambient temperature and the reaction mixture was stirred for another 4 hours. 3-Cyclopropylpropylamine (48.5 mg, 0.569 mmol) was then added to the reaction mixture which was stirred at ambient temperature overnight under nitrogen. The reaction mixture was washed by saturated sodium bicarbonate and brine solution, concentrated and purified by flash column chromatography to yield the product as a white solid (23 mg, 8.5% yield). 1H NMR (300 MHz, CDCl3) δ 10.2, 7.68-7.83, 7.72, 7.65, 7.63, 7.55, 7.36, 7.04, 3.95-4.02, 3.83-3.95, 3.50-3.68, 3.40-3.50, 3.26-3.38, 1.60-1.72, 1.17-1.30, 0.71-0.80, 0.44-0.50, −0.06-0.013. MS (ES+) m/z 477 (M+1).

후처리

  1. stirringwas stirred at ambient temperature overnight under nitrogen
  2. washThe reaction mixture was washed by saturated sodium bicarbonate and brine solution
  3. concentrationconcentrated
  4. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-37d7cbcd9f7640cc9d608dac98e3de00
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964591B2

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