1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid (2,2-diethoxy-ethyl)-amide

HRID 220752Notes

Reaction equation

HRID 220752 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([C:20](O)=[O:21])[CH:14]=2)=[CH:9][CH:8]=1)=[O:5].[CH2:28]([O:30][CH:31]([O:34][CH2:35][CH3:36])[CH2:32][NH2:33])[CH3:29].CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH2:28]([O:30][CH:31]([O:34][CH2:35][CH3:36])[CH2:32][NH:33][C:20]([C:15]1[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:26][CH:25]=[CH:24][C:23]=3[F:27])=[CH:8][CH:9]=2)[C:18]([CH3:19])=[CH:17][CH:16]=1)=[O:21])[CH3:29]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 695242,2-DiethoxyethylamineHCID 586837824'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid

Product 1

HCID 586837904'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid (2,2-diethoxy-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 1 was hydrolyzed by heating it in a solution of LiOH to yield 4′-(2,6-difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid. A mixture of 4′-(2,6-difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid (800 mg, 2.2 mmol), 2,2-diethoxy-ethylamine (0.32 mL, 2.2. mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (5 mmol) in dry DMF (5 mL) was stirred at room temperature for 24 h. The mixture was diluted with water (20 mL) and extracted with ethyl acetate (EtOAc) (2×20 mL). The organic extract was washed with water and dried. The oil obtained on concentration of the organic layer was purified by flash chromatograghed on silica gel to give 4′-(2,6-difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid (2,2-diethoxy-ethyl)-amide as colorless oil (0.68 g).

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (2×20 mL)
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. customThe oil obtained on concentration of the organic layer
  6. customwas purified by flash

Sources & evidence

ORD record
ord-c3d340c5a7604844a312bac120a9c89e
Source dataset
uspto-grants-2012_06
Patent number
US08202999B2

Reaction notes

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