Felbinac → HCID 24811002, compound

HRID 1945380Notes

Reaction equation

HRID 1945380 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.[CH3:17][O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:17][O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:8](=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][C:1]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:5]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 3332FelbinacHCID 757711-HydroxybenzotriazoleHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 24811002HCID 24811002, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 4-biphenyl acetic acid (106.1 mg, 0.50 mmol), 3-amino benzoic acid methyl ester (113.4 mg, 0.75 mmol), EDCHCl (143.8 mg, 0.75 mmol) and HOBT (101.4 mg, 0.75 mmol) were dissolved in DMF (5.0 mL), and DIPEA (0.13 mL, 0.75 mmol) were added. The reaction mixture was stirred at room temperature overnight and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (n-Hexane: Ethyl acetate:MeOH=6:3:1) gave 3-(2-biphenyl-4-yl-acetyl-amino)benzoic acid methyl ester as a white solid (174 mg, 100% yield).

Workup

  1. custompartitioned between Ethyl acetate and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane: Ethyl acetate:MeOH=6:3:1)

Sources & evidence

ORD record
ord-e26e86e4129543a3b062d3ac0dbb7f85
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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