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

HRID 2228161Notes

Reaction equation

HRID 2228161 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 sodiumlchloride 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. 1H-NMR (200 MHz, CDCl3) δ 1.53-1.85 (4H, m), 2.21 (3H, s), 2.38(3H, s), 2.54-2.72 (1H, m), 3.31-3.44 (2H, m), 3.56 (2H, s), 3.98-4.11 (2H, m), 6.52 (1H, d, J=15.4 Hz), 6.67-6.69 (2H, m), 7.22 (2H, d, J=8.0 Hz), 7.29 (2H, d, J=8.4 Hz), 7.41 (1H, s), 7.48-7.64 (5H, m).

Workup

  1. washand the mixture was washed with water and saturated sodiumlchloride 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-fb82171e8e74440480bc2bada2c4f702
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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