Water → HCID 86626121, compound

HRID 390689Notes

Reaction equation

HRID 390689 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:9][O:10]/[C:11](=[CH:16]\[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:42])[C:30](OC3C=CC([N+]([O-])=O)=CC=3)=[O:31])[CH:24]=2)=[CH:19][CH:18]=1)/[C:12]([O:14][CH3:15])=[O:13].O>CN(C)C=O>[CH2:1]([NH:8][C:30](=[O:31])[N:29]([C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17](/[CH:16]=[C:11](\[O:10][CH3:9])/[C:12]([O:14][CH3:15])=[O:13])=[CH:18][CH:19]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:42])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 81271-HeptanamineHCID 86626082HCID 86626082, compound

Product 1

HCID 86626121HCID 86626121, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.6 mL (3.9 mmol) of heptylamine is added to a solution of 1.7 g (3.2 mmol) of methyl (Z)-2-methoxy-3-{3′-[methyl-(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate (prepared according to Example 11e) in 10 mL of dimethylformamide and the reaction medium is then placed in a bath preheated to 80° C. After stirring at 80° C. for 3 hours, water is added and the reaction medium is extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 and then 6/4 heptane/ethyl acetate mixture. 1.1 g (80%) of methyl (Z)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylate are obtained in the form of a white solid with a melting point of 93° C.

Workup

  1. customthe reaction medium is then placed in a bath
  2. custompreheated to 80° C
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. washThe organic phase is washed with saturated aqueous sodium chloride solution
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 7/3

Sources & evidence

ORD record
ord-3bd15c1011e24b85b3156b6ea350ad35
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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