2,6-Dichloroquinoline-3-carboxylic acid → HCID 67357380, compound

HRID 2065705Notes

Reaction equation

HRID 2065705 reaction equation
Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[NH2:16][CH:17]([CH:21]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)[C:22]([OH:24])=[O:23])[C:18]([OH:20])=[O:19]>CS(C)=O>[C:12]([C:11]1[C:2]([NH:16][CH:17]([CH:21]([C:25]2[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=2)[C:22]([OH:24])=[O:23])[C:18]([OH:20])=[O:19])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([Cl:15])=[CH:6][CH:5]=2)([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 242660682,6-Dichloroquinoline-3-carboxylic acidHCID 67358437HCID 67358437, compound

Product 1

HCID 67357380HCID 67357380, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with 2-amino-3-(3,5-difluoro-phenyl)-succinic acid [prepared by analogy to J. Med. Chem. 1973, 16, 1277-1280.; using alkylation of diethyl acetamidomalonate by methyl bromo-(3,5-difluoro-phenyl)-acetate] in DMSO to provide the title compound in good yield.

Sources & evidence

ORD record
ord-d18fdf82451342c7a2cf78bffe95b24c
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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