4-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester → 4-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid

HRID 490405Notes

Reaction equation

HRID 490405 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:24])=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH:9]=1)=[O:4]>O1CCCC1>[C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]([NH:11][CH2:10][C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=2[CH3:24])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 588241954-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 184445844-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester (158) (91 mg, 0.283 mmoles) in dry tetrahydrofuran (5 ml) was treated with potassium trimethylsilanoate (182 mg, 1.42 mmoles) and the mixture stirred under an argon atmosphere for 3 hours. After evaporation of the solvent, the residue was purified by HPLC (gradient: 15% acetonitrile/85% water containing 0.1% trifluoroacetic acid to 55% acetonitrile/45% water at a rate of 1%/min) to afford compound 160 (35 mg) as a white solid. LC/MS System D; Rt=7.64 mins, m/z (ES+)=308 (M+H for C19H17NO3).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by HPLC (gradient

Sources & evidence

ORD record
ord-9abb4fe076f54318b23c52cee6826018
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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