Lithium Hydroxide → 4-(Benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylic acid

HRID 1918215Notes

Reaction equation

HRID 1918215 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[C:14]([C:26]([O:28]C)=[O:27])=[C:15]([C:18]2[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=2)[S:16][CH:17]=1)=[O:11].[OH-].[Li+]>O1CCCC1.CO.O.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[C:14]([C:26]([OH:28])=[O:27])=[C:15]([C:18]2[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=2)[S:16][CH:17]=1)=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67052227Methyl 4-(benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

Product 1

HCID 670523634-(Benzofuran-2-carboxamido)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The ester 161 and lithium hydroxide in tetrahydrofuran: methanol:water (3:2:1) is stirred at room temperature for 4 h. The mixture is diluted with DMF and purified by HPLC to provide 162.

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-327f33353a5e41e2a92697de9416d73c
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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