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ChemicalBook CAS DataBase List 1,1-Cyclopropanedicarboxamide,N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-N'-phenyl-
849221-94-9

1,1-Cyclopropanedicarboxamide,N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-N'-phenyl- synthesis

7synthesis methods
Cyclopropanecarboxylic acid, 1-[(phenylaMino)carbonyl]-

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190728-25-7 Synthesis
4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline

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1,1-Cyclopropanedicarboxamide,N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-N'-phenyl-

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-

Yield:-

Reaction Conditions:

Stage #1: 1-(phenylcarbamoyl)cyclopropane-1-carboxylic acidwith 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate;N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide; for 0.333333 h;
Stage #2: 4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline in N,N-dimethyl-formamide at 35; for 3 h;Molecular sieve;

Steps:

4

Add DMF, HCTU, and DIEA to the reaction flask at room temperature, and stir for 10 minutes. After adding Zhong 1 and stirring for another 20 minutes, then adding Zhong 2 again. After 3 hours of reaction, 14% of the raw material remained, and the temperature was raised to 35°C until the reaction was complete. Add 10L of water,The product is separated out and filtered to obtain the defluorinated impurity of cabozantinib with a purity of 99%. Among them, Intermediate 1: 334.5g; Intermediate 2: 400g; HCTU: 620g; DIEA: 387.7g; DMF (molecular sieve drying): 3.4L.

References:

CN111533690,2020,A Location in patent:Paragraph 0019; 0037-0038

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