1,4-Dioxane → HCID 178515407, compound

HRID 1158633Notes

Reaction equation

HRID 1158633 reaction equation
[Br:1][C:2]1[N:11]=[C:10]([C:12]#[N:13])[C:9]([OH:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH:25][NH2:26])=O)=[CH:18][CH:17]=1.O1CCOCC1>C(O)(=O)C>[Br:1][C:2]1[N:11]=[C:10]([C:12]2[NH:13][C:23]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)=[N:25][N:26]=2)[C:9]([OH:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 37716122-(4-Fluorophenyl)acetohydrazideHCID 86613115HCID 86613115, compound

Product 1

HCID 178515407HCID 178515407, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of 5-bromo-8-hydroxy-1,6-naphthyridine-7-carbonitrile (0.25 g, 9.99 mmol), 2-(4-fluorophenyl)acetic hydrazide (0.34 g, 2 mmol), 1,4-dioxane (2 mL) and acetic acid was heated at 200° C. for 10 minutes in a microwave chamber. The mixture was allowed to cool to room temperature, the precipitate was filtered and washed with dichloromethane. The filtrate was concentrated in vacuo, 1 N sodium hydroxide and ethyl acetate were added and the aqueous layer was washed with ethyl acetate. The aqueous layer was then acidified to pH 5 and the solids formed were collected. This material was azeotroped with methanol to provide 5-bromo-7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol (0.17 g, 42%) as a yellow solid. 1H NMR (CDCl3/CD3OD): δ 9.07 (dd, J=4.0, 1.2 Hz, 1 H), 8.50 (dd, J=8.4, 1.2 Hz, 1 H), 7.65 (dd, J=8.4, 4.0 Hz, 1 H), 7.26 (m, 2 H), 6.95 (m, 2 H), 4.11 (s, 2 H); MS m/z 400 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo, 1 N sodium hydroxide and ethyl acetate
  5. additionwere added
  6. washthe aqueous layer was washed with ethyl acetate
  7. customthe solids formed
  8. customwere collected
  9. customThis material was azeotroped with methanol

Sources & evidence

ORD record
ord-73bc1793456144f19102741d32d989eb
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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