5-Bromo-1,6-naphthyridin-2(1H)-one → 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one

HRID 542519Notes

Reaction equation

HRID 542519 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.[CH3:13][C:14]1[N:18]=[CH:17][NH:16][N:15]=1>CN1CCCC1=O>[CH3:13][C:14]1[N:18]=[CH:17][N:16]([C:2]2[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:12])[NH:7]3)[N:15]=1

Participants

4

Reactant 2

HCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one2×HCID 178433329HCID 178433329, compound

Product 1

HCID 102631315-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-oneYield 44.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 20 g of 3-methyl-1H-1,2,4-triazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170°-180° C. for 18 hours and then cooled to room temperature whereupon a tan solid crystallized out. The mixture was diluted by adding 125 ml of water and the separated solid was collected, washed with water, air-dried and combined with another 1.2 g sample of the same material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven at 95°-100° C. for three days to yield 6.1 g of 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300° C.

Workup

  1. temperaturewas heated in an oil bath at 170°-180° C. for 18 hours
  2. customcrystallized out
  3. additionThe mixture was diluted
  4. additionby adding 125 ml of water
  5. customthe separated solid was collected
  6. washwashed with water
  7. customair-dried
  8. customobtained in another run
  9. customThe combined solids were recrystallized from dimethylformamide
  10. customdried in an oven at 95°-100° C. for three days

Sources & evidence

ORD record
ord-ea6459e859654c91b7d423a304e3acf3
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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