2-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl ester → HCID 57762632, compound

HRID 1365694Notes

Reaction equation

HRID 1365694 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].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[N:26]([CH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)[C:27]1[CH:32]=[CH:31][C:30](OS(C(F)(F)F)(=O)=O)=[CH:29][CH:28]=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:30]1[CH:31]=[CH:32][C:27]([N:26]([C:21]2[N:20]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 577625182-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl esterHCID 57762604HCID 57762604, compound

Product 1

HCID 57762632HCID 57762632, compoundYield 59.2%

Procedure

In the same manner as in Example 1, 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (164.0 mg) was reacted with trifluoromethanesulfonic acid 4-[pyrimidin-2-yl-(tetrahydropyran-4-yl)amino]phenyl ester (220.0 mg) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(pyrimidin-2-yl-(tetrahydro-pyran-4-yl)-amino)phenyl]pent-4-enoic acid methyl ester (178.5 mg). Column chromatography (silica gel, eluent: chloroform/cyclohexane=1/2→chloroform) and thin layer chromatography (silica gel, developing solvent: cyclohexane/ethyl acetate=1/1) were used for purification.

Sources & evidence

ORD record
ord-2e5c2e729199476bb22b737da419e8a6
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Reaction notes

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