Dimethylformamide → HCID 15293174, compound

HRID 128938Notes

Reaction equation

HRID 128938 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.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:26]N(C=O)C>>[CH2:18]([N:25]1[CH:26]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]1=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7504BenzylamineHCID 54500696HCID 54500696, compound

Product 1

HCID 15293174HCID 15293174, compoundYield 51%

Procedure

To a solution of 8-phenylpyrano [3,4-b]pyridin-5-one (100 mg, 0.45 mmoles) in 5 ml DMF was added benzylamine (0,006 ml, 0.54 mmoles) under nitrogen. The reaction mixture was heated overnight to 80° C., cooled and concentrated under vacuum to give 253 mg of crude product. The crude product was chromatographed eluting with 1:1 EtOAc/Hexanes to give 72 mg (51% yield) of the desired 6-benzyl-8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 166°-167° C.; 1H NMR (CDCl3, 300 MHz) δ5.31 (s, 2H), 7.28-7.58 (m, 12H) 8.82 (dd, 1H, J=8.2, 1.8 Hz) 8.98 (dd, 1H, J=4.6, 2.0 Hz); 13C NMR (75 MHz, CDCl3) δ161.88, 154.10, 151.84, 137.00, 136.29, 135.06, 134.24, 130.02, 129.02, 128.40, 128.19,128.12, 127.77, 122.06, 121.09,120.99, 52.00; mass spectrum (CI) , m/e 312; exact mass calcd. for C21H16N2O 312.1263, found 312.1259.

Workup

  1. temperatureThe reaction mixture was heated overnight to 80° C.
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. customto give 253 mg of crude product
  5. customThe crude product was chromatographed
  6. washeluting with 1:1 EtOAc/Hexanes

Sources & evidence

ORD record
ord-e0d783779cdb4e709e7c84d8146c152c
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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