Triethylamine → HCID 18472291, compound

HRID 1277145Notes

Reaction equation

HRID 1277145 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:19][N:20]([CH2:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)[CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C=O)C>[CH3:19][N:20]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([NH:32][C:16](=[O:18])/[CH:15]=[CH:14]/[C:10]2[CH:11]=[N:12][CH:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[CH:9]=2)=[CH:33][CH:34]=1)[CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 18472468HCID 18472468, compound

Product 1

HCID 18472291HCID 18472291, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-[5-(4-methylphenyl)pyridin-3-yl]acrylic acid (150 mg), 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (168 mg) and triethylamine (0.10 ml) in DMF (10 ml) was added diethyl cyanophosphate (0.12 ml) at 0° C., and the mixture was stirred at room temperature for 3 hours and concentrated under reduced pressure. To the residue was added water, the mixture was extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:2) to give (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-methylphenyl)pyridin-3-yl]acrylic amide (Compound 215) (24 mg) as yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified with column chromatography (ethanol/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-e79c277ca43e4df58e5de358f7348e95
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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