2-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid → HCID 44250489, compound

HRID 1964054Notes

Reaction equation

Cl.[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH2:11])=[CH:3]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[CH2:24][O:25][CH2:26][C:27](O)=[O:28])=[C:18]([C:31]([O:33]C)=[O:32])[CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[CH2:24][O:25][CH2:26][C:27]([NH:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[C:7]([C:4]3[CH:5]=[CH:6][O:2][CH:3]=3)[CH:8]=2)=[O:28])=[C:18]([CH:17]=1)[C:31]([OH:33])=[O:32]

Participants

Reactant 2

HCID 510399542-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid

HCID 66877446HCID 66877446, compound

Product 1

HCID 44250489HCID 44250489, compound

Procedure

Using the same method as in Example 1-(ii), 3-(furan-3-yl)benzylamine.hydrochloride was reacted with the (2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethoxy)acetic acid obtained in Example 1-(i) to give 5-chloro-2-([(2-([3-(furan-3-yl)benzyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 77%). Note that 3-(furan-3-yl)benzylamine.hydrochloride was neutralized in DMA by adding an equivalent amount of triethylamine, and then used in the reaction.

Sources & evidence

ORD record: ord-19a7c842137945fd877e9eda41e010b0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415479B2

Reaction notes

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