Sodium hydride → HCID 66660151, compound

HRID 1383858Notes

Reaction equation

HRID 1383858 reaction equation
Cl[C:2]1[C:3]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.[CH3:22][N:23]1[CH:27]=[N:26][C:25]([CH2:28][OH:29])=[N:24]1.[H-].[Na+]>CN(C=O)C.O>[CH2:18]([N:17]([CH2:20][CH3:21])[C:3]1[C:2]([O:29][CH2:28][C:25]2[N:26]=[CH:27][N:23]([CH3:22])[N:24]=2)=[N:7][N:6]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=[C:5]2[CH:4]=1)[CH3:19]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanolHCID 21187511HCID 21187511, compound

Product 1

HCID 66660151HCID 66660151, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(6-chloro-3-phenyl-1,2,4-triazolo[4,3-b]pyridazin-7-yl)-N,N-diethylamine (180 mg, 0.33 mmol) and (1-methyl-1 H-1,2,4-triazol-3-yl)methanol (68 mg) in dry DMF (5 ml) was added sodium hydride (60% dispersion in oil, 34 mg, 0.36 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (50 ml) and extracted with dichloromethane (3×25 ml). The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated. The solid was recrystallised from ethyl acetate, and collected by filtration to afford the title pyridazine (81 mg, 36%). 1H NMR (500 MHz, DMSO-d6) δ1.08 (6 H, t, J=8.5 Hz), 3.31 (4 H, q, J=8.5 Hz), 3.87 (3 H, s), 5.50 (2 H, s), 7.22 (1 H, s), 7.47-7.59 (3 H, m), 8.37 (2 H, d, J=8.5 Hz), 8.51 (1 H, s). MS (ES+) 379 [MH]+.

Workup

  1. extractionextracted with dichloromethane (3×25 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid was recrystallised from ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e99e6207623e4ad69b30b07cc875ee28
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

Loading…