Water → HCID 67272544, compound

HRID 250928Notes

Reaction equation

HRID 250928 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:29])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH:15]=1.I[CH2:31][CH2:32][CH2:33][CH3:34].C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:31]([NH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:29])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH:15]=1)[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 81531DiisopropylethylamineHCID 67273349HCID 67273349, compound

Product 1

HCID 67272544HCID 67272544, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 mg (0.5 mmol, 1 eq) of methyl 3-[2-amino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate (prepared in Example 52c) and 60 μL (0.55 mmol, 1.1 eq) of 1-iodobutane in 2 ml of dimethylformamide in the presence of 170 μL (10.5 mmol, 2.1 eq) of diisopropylethylamine is heated at 80° C. for 16 hours. The reaction medium is hydrolyzed with water and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residue is chromatographed on silica gel (70/30 heptane/ethyl acetate). 114.8 mg of methyl 3-[2-butylamino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained in the form of a yellow oil. Yield=51%

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residue is chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-bd8637ce26fa4eacb7f5085be6622259
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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