Dimethylformamide → HCID 19373032, compound

HRID 128939Notes

Reaction equation

HRID 128939 reaction equation
[C:1]1([CH:7]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:17])CO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.[CH3:26]N(C=O)C>>[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[CH:26]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10]2=[O:17])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 773174-PyridinemethanamineHCID 54500696HCID 54500696, compound

Product 1

HCID 19373032HCID 19373032, compoundYield 48%

Procedure

To a solution of 8 -phenylpyrano [3,4-b]pyridin-5-one (102 mg, 0.46 mmoles) in 2 ml DMF was added 4-picolylamine (0.055 ml, 0.55 mmoles) under nitrogen. The reaction mixture was heated overnight to 80° C., cooled and then concentrated under vacuum to give 0,335 g crude product which was chromatographed eluting with 1:1 ethyl acetate/hexanes to give 69 mg (48% yield) of the desired 6-(4-pyridylmethyl)-8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 199.5°-200.5° C.; 1H NMR (CDCl3,300 MHz) δ5.30 (s, 2H), 7.26 (d, 2H, J=6), 7.34-7.59 (m, 7H), 8.6 (d, 2H, J=6), 8.78 (dd, 1H, J=8.04, 2.00), 8.99 (dd, 1H, J=4.39, 1.83); 13C NMR (75 MHz, CDCl3) δ161.90, 154.52, 152.09, 150.08, 145.44, 136.72, 134.77, 133.67, 129.96, 128.40, 127.92, 122.44, 122.16, 121.90, 121.81, 51.18; IR (KBr) vmax 3445, 1655, 1624, 1599, 1437, 1421, 1373, 1169, 1099, 993,922, 868, 794, 763, 727, 707, 677, 607, 598, 522 cm-1 ; mass spectrum (EI), m/e 313. Anal. (C20H15N3O 3/4 H2O) Calcd.: C, 73.49; H, 5.09; N, 12.86. Found: C, 73.73; H, 4.99; N, 12.36.

Workup

  1. temperatureThe reaction mixture was heated overnight to 80° C.
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. customto give 0,335 g crude product which
  5. customwas chromatographed
  6. washeluting with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-77f50c31eef441379ec651f2016de480
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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