3-Aminopyridine → 5-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623812Notes

Reaction equation

HRID 1623812 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:41]([C:44]1[CH:45]=[CH:46][C:47]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:48]([CH:52]=1)[C:49](O)=[O:50])(=[O:43])[CH3:42]>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O.C(OCC)(=O)C>[C:41]([C:44]1[CH:45]=[CH:46][C:47]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:48]([CH:52]=1)[C:49]([NH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:50])(=[O:43])[CH3:42]

Participants

9

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218806135-Acetyl-2-(benzyloxy)benzoic acid

Product 1

HCID 671072525-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Diisopropylethylamine (0.97 ml, 5.55 mmol), 3-aminopyridine (418 mg, 4.44 mmol) and HATU (1.27 g, 3.33 mmol) were added to a solution of 5-acetyl-2-[(phenylmethyl)oxy]benzoic acid (commercially available from Acros; 600 mg, 2.22 mmol) in dimethylformamide (10 ml). The solution was stirred for 2 hours. Ethyl acetate (40 ml) and H2O (40 ml) were added and the organic layer washed with H2O (3×20 ml), dried and the solvent removed in vacuo to give a solid. Trituration with 3:1 hexane/ethyl acetate yielded the title compound as a yellow solid. 541 mg.

Workup

  1. washthe organic layer washed with H2O (3×20 ml)
  2. customdried
  3. customthe solvent removed in vacuo
  4. customto give a solid

Sources & evidence

ORD record
ord-5e16427e51254d8c96db2d14f471f0d7
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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