Sodium hydride → 7-(1,1-Dimethylethyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-1,2,4-triazolo(4,3-b)pyridazine

HRID 986914Notes

Reaction equation

HRID 986914 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[N:6][CH:5]=[N:4]1)[CH3:2].Cl[C:11]1[C:12]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:13][C:14]2[N:15]([C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[N:18][N:19]=2)[N:16]=1.[H-].[Na+]>CN(C=O)C.O>[CH3:30][C:27]([C:12]1[C:11]([O:9][CH2:8][C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][N:6]=2)=[N:16][N:15]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[N:18][N:19]=[C:14]2[CH:13]=1)([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 111508847-Tert-butyl-6-chloro-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 99086847-(1,1-Dimethylethyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-1,2,4-triazolo(4,3-b)pyridazineYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-ethyl-2H-1,2,4-triazol-3-yl)methanol (0.094 g, 0.74 mmol) and 6-chloro-7-(1,1-dimethylethyl)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine (0.15 g. 0.49 mmol) in DMF (10 ml) was added sodium hydride (0.024 g of a 60% dispersion in oil, 1.1 mol eq.) and the reaction mixture was stirred at room temperature for 30 minutes. After this time, the reaction mixture was diluted with water (80 ml) and the solid that precipitated was collected by filtration and washed several times with water in the sinter funnel. The solid was recrystallised from ethyl acetate/hexane to give pure title compound (0.085 g, 44%). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ1.40-1.47 (12H, m), 4.14 (2H, t, J=7.3 Hz), 5.26 (2H, s), 7.26-7.38 (2H, m), 7.53-7.58 (1H, m), 7.86-7.90 (1H, m), 7.93 (1H, s), 7.99 (1H, s); MS (ES+) m/e 396 [MH]+. Anal. Found C, 61.02; H, 5.45; N, 24.75%. C20H22FN7O requires C, 60.75; H, 5.61; N, 24.79%.

Workup

  1. customthe solid that precipitated
  2. filtrationwas collected by filtration
  3. washwashed several times with water in the sinter funnel
  4. customThe solid was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4eb6d2d7b25b4525bfc187de130b2887
Source dataset
uspto-grants-2003_10
Patent number
US06630471B1

Reaction notes

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