Triethylamine → HCID 136146730, compound

HRID 1718847Notes

Reaction equation

HRID 1718847 reaction equation
[CH3:1][C:2]1[N:3]([C:31]2[CH:42]=[CH:41][C:34]([O:35][CH:36]([CH3:40])[C:37]([NH2:39])=O)=[CH:33][CH:32]=2)[C:4](=[O:30])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][C:27](=[O:29])[O:26][N:25]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>C(#N)C.O>[CH3:1][C:2]1[N:3]([C:31]2[CH:32]=[CH:33][C:34]([O:35][CH:36]([CH3:40])[C:37]#[N:39])=[CH:41][CH:42]=2)[C:4](=[O:30])[C:5]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][C:27](=[O:29])[O:26][N:25]=3)=[CH:16][CH:17]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 136146861HCID 136146861, compound

Product 1

HCID 136146730HCID 136146730, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-{4-[2-methyl-6-oxo-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-4-propylpyrimidin-1(6H)-yl]phenoxy}propanamide (0.57 g) and triethylamine (0.42 mL) in acetonitrile (5 mL) was added trifluoroacetic anhydride (0.28 mL), and the mixture was stirred for 12 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.35 g, 64%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-751e326c3d3241cf93be79bea3c3f1ab
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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