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Sodium hydride → 3-(2,5-Difluorophenyl)-7-(1,1-dimethylethyl)-6-((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)-1,2,4-triazolo(4,3-b)pyridazine

HRID 2301336
Notes
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Reaction equation

HRID 2301336 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[N:5][CH:4]=[N:3]1.Cl[C:10]1[C:11]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:12][C:13]2[N:14]([C:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])=[N:17][N:18]=2)[N:15]=1.[H-].[Na+]>CN(C=O)C.O>[F:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[C:16]1[N:14]2[N:15]=[C:10]([O:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[CH:4][N:5]=3)[C:11]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:12][C:13]2=[N:18][N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 112557487-tert-Butyl-6-chloro-3-(2,5-difluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 99088803-(2,5-Difluorophenyl)-7-(1,1-dimethylethyl)-6-((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)-1,2,4-triazolo(4,3-b)pyridazineYield 71.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-methyl-2H-1,2,4-triazol-3-yl)methanol (0.069 g, 0.4 mmol) and 6-chloro-3-(2,5-difluorophenyl)-7-(1,1-dimethylethyl)-1,2,4-triazolo[4,3-b]pyridazine (0.10 g, 0.31 mmol) in DMF (10 ml) was added sodium hydride (0.015 g of a 60% dispersion in oil, 1.2 mol eq.) and the reaction mixture was stirred at room temperature for 40 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 (0.088 g, 65%). Data for the title compound: 1H NMR (360 MHz, CDCl3) δ1.41 (9H, s), 3.89 (3H, s), 5.54 (2H, s), 7.23-7.26 (2H, m), 7.64 (1H, m), 7.91 (1H, s), 8.00 (1H, s); MS (ES+) m/e 400 [MH]+. Anal. Found C, 57.36; H, 4.61; N, 24.60%. C19H19F2N7O requires C, 57.14; H, 4.79; N, 24.55%.

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-510126639d504680a5fe74d968f2ef9c
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06500828B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes