2-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl ester → HCID 57762583, compound

HRID 1365690Notes

Reaction equation

HRID 1365690 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].Br[C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH2:34][C:35]2[N:36]=[CH:37][S:38][CH:39]=2)[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:26]=[CH:25][C:24]([N:27]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:34][C:35]2[N:36]=[CH:37][S:38][CH:39]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 577625182-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl esterHCID 57762605HCID 57762605, compound

Product 1

HCID 57762583HCID 57762583, compoundYield 59.8%

Procedure

In the same manner as in Example 1, 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (78.0 mg) was reacted with N-(4-bromophenyl)-N-((thiazol-4-yl)methyl)pyrimidin-2-amine (90.0 mg) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(pyrimidin-2-yl-thiazol-4-ylmethyl-amino)phenyl]pent-4-enoic acid methyl ester (87.7 mg). Column chromatography (silica gel, eluent: chloroform→chloroform/ethyl acetate=3/1) and thin layer chromatography (cyclohexane/ethyl acetate=1/2) were used for purification.

Sources & evidence

ORD record
ord-1cfee5e770b0401884edc47f189111f6
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Reaction notes

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