Benzaldehyde → HCID 67272052, compound

HRID 250929Notes

Reaction equation

HRID 250929 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.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([BH3-])#N.[Na+].[Cl-].[NH4+]>CO>[CH2:30]([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)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 67273349HCID 67273349, compound

Product 1

HCID 67272052HCID 67272052, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 72 μL (0.70 mmol, 1.4 eq) of benzaldehyde in 4 ml of methanol in the presence of 63 mg (1.0 mmol, 2 eq) of sodium cyanoborohydride is stirred at room temperature for 16 hours. The reaction medium is hydrolyzed with ammonium chloride solution 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). 144 mg of methyl 3-[2-benzylamino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained in the form of a colorless oil. Yield=59%

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-5dfbd1ae93f54896a5284e3a0bd54bcd
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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