3-Hydroxy-thiophene-2-carboxylic acid methyl ester → 3-{2-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetoxy}-thiophene-2-carboxylic acid methyl ester

HRID 348454Notes

Reaction equation

HRID 348454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]([C:26]1[S:27][CH:28]=[CH:29][C:30]=1O)=[O:25]>CO.ClCCl>[CH3:22][O:23][C:24]([C:26]1[S:27][CH:28]=[CH:29][C:30]=1[O:20][C:19](=[O:21])[CH2:18][O:17][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:16][N:15]=1)=[O:25]

Participants

4

Reactant 2

HCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl esterHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 695241313-{2-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetoxy}-thiophene-2-carboxylic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 3-hydroxy-thiophene-2-carboxylic acid methyl ester (20 mg, 0.13 mmol) as the source alcohol. Chromatography (5% methanol/dichloromethane) through SiO2 yielded 32 mg (44%) of the titled compound. ESI-MS m/z 432 (MH+), 430 (M−H−).

Sources & evidence

ORD record
ord-4b739139ebd24e4b9e8c3cbe4a85b0f6
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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