2,6-Dichloroquinoline-3-carboxylic acid → HCID 67358741, compound

HRID 2065715Notes

Reaction equation

HRID 2065715 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][C@@H:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[N:32][CH:33]=[C:34]([Br:39])[CH:35]=3)[N:30]=2)=[CH:24][CH:23]=1)[C:18]([OH:20])=[O:19]>CS(C)=O>[Br:39][C:34]1[CH:35]=[C:36]2[C:31](=[N:32][CH:33]=1)[N:30]=[C:29]([O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@H:17]([NH:16][C:2]3[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=4)[N:3]=3)[C:18]([OH:20])=[O:19])=[CH:27][CH:26]=1)[CH:38]=[CH:37]2

Participants

4

Reactant 2

HCID 242660682,6-Dichloroquinoline-3-carboxylic acidHCID 67360868HCID 67360868, compound

Product 1

HCID 67358741HCID 67358741, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In close analogy to the procedure described in Example 109c, 2,6-dichloroquinoline-3-carboxylic acid is reacted with (S)-2-amino-3-[4-(6-bromo-[1,8]naphthyridin-2-yloxy)-phenyl]-propionic acid (prepared by analogy to Example 109a,b) in DMSO to provide the title compound in good yield.

Sources & evidence

ORD record
ord-d622b3f76dd84124add4db14adb168a3
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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