Triethylamine → (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-methylphenyl)furan-2-yl]acrylic amide

HRID 1387899Notes

Reaction equation

HRID 1387899 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]([CH2:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)[CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C=O)C.C(OCC)(=O)C>[CH3:18][N:19]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([NH:31][C:15](=[O:17])/[CH:14]=[CH:13]/[C:11]2[O:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)=[CH:32][CH:33]=1)[CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 626428262806-32-0HCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine

Product 1

HCID 18472421(E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-methylphenyl)furan-2-yl]acrylic amideYield 23.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-[5-(4-methylphenyl)furan-2-yl]acrylic acid (200 mg), 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (212 mg) and triethylamine (0.15 ml) in DMF (10 ml) was added diethyl cyanophosphate (0.16 ml) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the mixture was added ethyl acetate, and the mixture was washed with water and saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:50→1:25→1:10) to give (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-methylphenyl)furan-2-yl]acrylic amide (Compound 210) (87 mg) as brown amorphous.

Workup

  1. washthe mixture was washed with water and saturated sodium chloride solution
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was separated
  5. custompurified with column chromatography (ethanol/ethyl acetate=1:50→1:25→1:10)

Sources & evidence

ORD record
ord-457ba1db90504cb1a7fd825b5b22c230
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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