Triethylamine → HCID 136146730, compound

HRID 1674177Notes

Reaction equation

HRID 1674177 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-5593d9af42104f7b8405de34cb4db7fc
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

Loading…