2-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl ester → HCID 57762569, compound

HRID 230351Notes

Reaction equation

HRID 230351 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].I[C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH2:34][CH2:35][C:36]#[N:37])[C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:23][CH:22]=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:21]1[CH:22]=[CH:23][C:24]([N:27]([CH2:34][CH2:35][C:36]#[N:37])[C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 577625182-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl esterHCID 57762584HCID 57762584, compound

Product 1

HCID 57762569HCID 57762569, compoundYield 78.9%

Procedure

In the same manner as in Example 1, 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (73 mg) was reacted with 3-(N-(4-iodophenyl)-N-(pyrimidin-2-yl)amino)propanenitrile (94 mg) to obtain (E)-5-[4-((2-cyano-ethyl)-pyrimidin-2-yl-amino)-phenyl]-2-(2,6-dichlorobenzamido)-pent-4-enoic acid methyl ester (100 mg). Column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/2→1/5) was used for purification.

Sources & evidence

ORD record
ord-2d5e1193ff4c4cf8ae8773d6d1e594d2
Source dataset
uspto-grants-2009_07
Patent number
US07566724B2

Reaction notes

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