8-Quinolineboronic acid → HCID 44251376, compound

HRID 1964023Notes

Reaction equation

HRID 1964023 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2B(O)O)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:16]=[CH:17][C:18]([CH3:40])=[C:19]([NH:21][C:22](=[O:39])[CH2:23][O:24][CH2:25][C:26]([NH:28][C:29]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:30]=2[C:31]([OH:33])=[O:32])=[O:27])[CH:20]=1>>[Cl:38][C:35]1[CH:36]=[CH:37][C:29]([NH:28][C:26](=[O:27])[CH2:25][O:24][CH2:23][C:22]([NH:21][C:19]2[CH:20]=[C:15]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[N:1]=[CH:2][CH:3]=[CH:4]4)[CH:16]=[CH:17][C:18]=2[CH3:40])=[O:39])=[C:30]([CH:34]=1)[C:31]([OH:33])=[O:32]

Participants

3

Reactant 2

HCID 27343808-Quinolineboronic acidHCID 86653350HCID 86653350, compound

Product 1

HCID 44251376HCID 44251376, compound

Procedure

Using the same method as in Example 19-(ii), 8-quinoline boronic acid was reacted with the 2-[((2-[(5-bromo-2-methylphenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid.methyl ester obtained in Example 38-(i) to give 5-chloro-2-([(2-([2-methyl-5-(quinolin-8-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 53%).

Sources & evidence

ORD record
ord-e300598d8aba4da7b8e724560dea7e60
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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