6-Aminoquinoline → (2S,4EZ)-4-benzylidene-1-[4-(dimethylamino)butanoyl]-N-(6-quinolinyl)-2-pyrrolidinecarboxamide

HRID 1349057Notes

Reaction equation

HRID 1349057 reaction equation
[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15]C(C)(C)C)=O)[C@H:10]([C:20]([OH:22])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:31])[CH2:25][CH2:26][CH2:27]C(Cl)=O.[N:32]1[C:41]2[C:36](=[CH:37][C:38]([NH2:42])=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>>[CH:1](=[C:8]1[CH2:12][N:11]([C:13](=[O:15])[CH2:27][CH2:26][CH2:25][N:24]([CH3:31])[CH3:23])[C@H:10]([C:20]([NH:42][C:38]2[CH:37]=[C:36]3[C:41](=[CH:40][CH:39]=2)[N:32]=[CH:33][CH:34]=[CH:35]3)=[O:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 113736-AminoquinolineHCID 150876904-(Dimethylamino)butanoyl chlorideHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69251275(2S,4EZ)-4-benzylidene-1-[4-(dimethylamino)butanoyl]-N-(6-quinolinyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 4-(dimethylamino)butanoyl chloride, and 6-quinolinamine the title compound was obtained in 71% purity by LC/MS. MS(ESI+): m/z=443.6.

Sources & evidence

ORD record
ord-28bd9a19fa9144469ff5f565c0322160
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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