Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-N'-phenylcyclopropane-1,1-dicarboxamide

HRID 2095887노트

반응식

HRID 2095887 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:13]=[C:14]([NH:16][C:17]([CH:19]4[CH2:21][CH2:20]4)=[O:18])[N:15]=3)[CH:12]=2)=[CH:4][CH:3]=1.[C:24]1([NH:30][C:31]([C:33]2([C:36](O)=[O:37])[CH2:35][CH2:34]2)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH:19]1([C:17]([NH:16][C:14]2[N:15]=[C:10]3[CH:9]=[CH:8][C:7]([O:6][C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:36]([C:33]5([C:31]([NH:30][C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)=[O:32])[CH2:35][CH2:34]5)=[O:37])=[CH:3][CH:4]=4)=[CH:12][N:11]3[CH:13]=2)=[O:18])[CH2:20][CH2:21]1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidHCID 58158625N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

생성물 1

HCID 58158573N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-N'-phenylcyclopropane-1,1-dicarboxamide수율 57%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of N-[6-(4-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (142 mg, 0.461 mmol) in N,N-dimethylacetamide (2.8 mL) were added 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (142 mg, 0.691 mmol), HATU (263 mg, 0.691 mmol) and N,N-diisopropylethylamine (120 μL, 0.691 mmol), and the mixture was stirred at room temperature for 4 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/60→0/100), washed with hexane/ethyl acetate and collected by filtration to give the title compound (130 mg, 57%) as a white solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/60→0/100)
  7. washwashed with hexane/ethyl acetate
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-89d9580caf2a4e95bfb73540c9d26e8d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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