2-Pyridinemethanamine → HCID 9856928, compound

HRID 896286Notes

Reaction equation

HRID 896286 reaction equation
[OH:1][C:2]1[C:3]([C:12]([O:14]C)=O)=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][NH2:23]>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]([C:12]([NH:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)=[O:14])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 22346294Methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 9856928HCID 9856928, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate from Example 1, Step 2 (0.05 g, 0.245 mmol) in dry toluene (3 mL) was added 1-pyridin-2-ylmethanamine (0.029 g, 0.270 mmol) and the mixture was heated to reflux for 16 hours. The solution was reduced to a smaller volume and refluxed for 4 additional hours. The solvent was removed under reduced pressure and the residue redissolved in DMF and filtered and the solution was purified by preparative HPLC (Gilson semipreparative HPLC system and a YMC Combiprep Column (50×20 mm I.D., C18, S-5 uM, 120 A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperaturerefluxed for 4 additional hours
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue redissolved in DMF
  6. filtrationfiltered
  7. customthe solution was purified by preparative HPLC (Gilson semipreparative HPLC system
  8. washa YMC Combiprep Column (50×20 mm I.D., C18, S-5 uM, 120 A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-b12d70dc72d642d18186bf16527035c4
Source dataset
uspto-grants-2005_07
Patent number
US06919351B2

Reaction notes

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