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

HRID 1786630Notes

Reaction equation

HRID 1786630 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-ab09486afca74d20a134ba0fe5071a3c
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

Loading…