1,1'-Carbonyldiimidazole → N-(1-Methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea maleate

HRID 4226

반응식

HRID 4226 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13].[C:24]1([S:30]([CH2:33][CH2:34][NH:35][CH:36]([CH3:38])[CH3:37])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>O1CCCC1.CO>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[CH3:37][CH:36]([N:35]([CH2:34][CH2:33][S:30]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:31])=[O:32])[C:12]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]1)=[O:13])[CH3:38]

참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 444266Maleic AcidHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

생성물 1

HCID 14050290N-(1-Methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea maleate수율 68.8%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 6.00 g (0.035 mole) of 1-(3-aminopropyl)-4-methylpiperazine and 6.97 g (0.043 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.17 g (0.036 mole) of N-(2-phenylsulfonylethyl)-2-propanamine in 100 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and water. The solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. The oil was dissolved in methanol; a solution of two equivalents of maleic acid in methanol was added, and a white solid precipitated. This was collected to give 15.48 g (68.8%) of white crystalline solid; m.p. 162°-163° C. with decomposition.

후처리

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customa white solid precipitated
  8. customThis was collected

출처 및 근거

ORD 기록
ord-54b66e4802a3406cb2dc05cb341eaba1
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04724235

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