6-Aminoquinoline → (2S,4EZ)-4-{[(3,4-dichlorobenzyl)oxy]imino}-1-[4-(dimethylamino)butanoyl]-N-(6-quinolinyl)-2-pyrrolidinecarboxamide

HRID 1349084Notes

Reaction equation

HRID 1349084 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])(C)(C)C.[CH3:27][N:28]([CH3:35])[CH2:29][CH2:30][CH2:31]C(Cl)=O.[N:36]1[C:45]2[C:40](=[CH:41][C:42]([NH2:46])=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1>>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[CH2:15][O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6](=[O:7])[CH2:31][CH2:30][CH2:29][N:28]([CH3:35])[CH3:27])[C@H:9]([C:24]([NH:46][C:42]2[CH:41]=[C:40]3[C:45](=[CH:44][CH:43]=2)[N:36]=[CH:37][CH:38]=[CH:39]3)=[O:26])[CH2:10]1

Participants

4

Reactant 3

HCID 113736-AminoquinolineHCID 150876904-(Dimethylamino)butanoyl chlorideHCID 131725417(2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725461(2S,4EZ)-4-{[(3,4-dichlorobenzyl)oxy]imino}-1-[4-(dimethylamino)butanoyl]-N-(6-quinolinyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid, 4-(dimethylamino)butanoyl chloride, and 6-quinolinamine the title compound was obtained in 95% purity by LC/MS. MS(ESI+): m/z=542.6.

Sources & evidence

ORD record
ord-e91d1b38f5db43e09ab478a5f8a8e882
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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