3-Aminopyridine → HCID 86668210, compound

HRID 1623807Notes

Reaction equation

HRID 1623807 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.[CH:41]([C:43]1[CH:44]=[CH:45][C:46]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:47]([CH:51]=1)[C:48](O)=[O:49])=[O:42]>CN(C)C=O.O.C(OCC)(=O)C>[CH:41]([C:43]1[CH:44]=[CH:45][C:46]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:47]([CH:51]=1)[C:48]([NH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:49])=[O:42]

Participants

8

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9698702-(Benzyloxy)-5-formylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86668210HCID 86668210, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylethylamine (0.95 ml, 5.46 mmol), 3-aminopyridine (514 mg, 5.46 mmol) and HATU (1.56 g, 4.1 mmol) were added to a solution of 5-formyl-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 97; 770 mg, 2.73 mmol) in dimethylformamide (10 ml). The solution was stirred for 72 hours. Ethyl acetate (40 ml) and H2O (40 ml) were added and the organic layer was washed with H2O (3×20 ml), dried and the solvent removed in vacuo to give a solid. The solid was purified by column chromatography (ethyl acetate) to yield the title compound as a white solid (300 mg).

Workup

  1. washthe organic layer was washed with H2O (3×20 ml)
  2. customdried
  3. customthe solvent removed in vacuo
  4. customto give a solid
  5. customThe solid was purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-869323fc556f4620bb487dcb35cb746d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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