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

HRID 2424512ノート

反応式

HRID 2424512 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

[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).

後処理

  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

出典と根拠

ORDレコード
ord-37d7cbcd9f7640cc9d608dac98e3de00
出典データセット
uspto-grants-2011_06
特許番号
US07964591B2

反応ノート

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