2-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl ester → HCID 57762611, compound

HRID 230360Notes

Reaction equation

HRID 230360 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:8][C:9](=[O:18])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[CH2:5][CH:6]=[CH2:7].[CH:20]1([CH2:23][N:24]([C:31]2[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=2)[C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:22][CH2:21]1>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:8][C:9](=[O:18])[C:10]1[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5]/[CH:6]=[CH:7]/[C:34]1[CH:35]=[CH:36][C:31]([N:24]([CH2:23][CH:20]2[CH2:21][CH2:22]2)[C:25]2[N:26]=[CH:27][CH:28]=[CH:29][N:30]=2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 577625182-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl esterHCID 57762541HCID 57762541, compound

Product 1

HCID 57762611HCID 57762611, compoundYield 69.1%

Procedure

In the same manner as in Example 1, 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (139 mg) was reacted with N-(cyclopropylmethyl)-N-(4-iodophenyl)pyrimidin-2-amine (162 mg) to obtain (E)-5-[4-(cyclopropylmethyl-pyrimidin-2-ylamino)phenyl]-2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (167 mg). Column chromatography (silica gel, eluent: hexane/ethyl acetate=1/1) was used for purification.

Sources & evidence

ORD record
ord-7e8546ab06784ecfba29f661260ed97e
Source dataset
uspto-grants-2009_07
Patent number
US07566724B2

Reaction notes

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