Sodium hydride → 7-(Tert-butyl)-3-(2,6-difluorophenyl)-6-((1-ethyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 2301338Notes

Reaction equation

HRID 2301338 reaction equation
Cl[C:2]1[C:3]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][C:5]2[N:6]([C:8]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[F:18])=[N:9][N:10]=2)[N:7]=1.[CH2:23]([N:25]1[C:29]([CH2:30][OH:31])=[N:28][CH:27]=[N:26]1)[CH3:24].[H-].[Na+]>CN(C=O)C>[F:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[C:8]1[N:6]2[N:7]=[C:2]([O:31][CH2:30][C:29]3[N:25]([CH2:23][CH3:24])[N:26]=[CH:27][N:28]=3)[C:3]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][C:5]2=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanolHCID 183724156-Chloro-3-(2,6-difluorophenyl)-7-(1,1-dimethylethyl)-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 98879547-(Tert-butyl)-3-(2,6-difluorophenyl)-6-((1-ethyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from 6-chloro-3-(2,6-difluorophenyl)-7-(1,1-dimethylethyl)-1,2,4-triazolo[4,3-b]pyridazine and (2-ethyl-2H-1,2,4-triazol-3-yl)methanol following the procedure (sodium hydride, DMF) described in WO 98/04559. Data for the title compound: m.p. 182° C.; 1H NMR (400 MHz, CDCl3) δ1.39-1.45 (12H, m), 4.10-4.16 (2H, m), 5.46 (2H, s), 7.09-7.15 (2H, m), 7.52-7.59 (1H, m), 7.92 (1H, s), 8.00 (1H, s); MS (ES30) m/e 414 [MH]+; Anal. Found: C, 58.19; H, 5.05; N, 23.80%. C20H21F2N7O requires: C, 58.10; H, 5.12; N, 23.72%.

Sources & evidence

ORD record
ord-8b7647e44b0c487fbf0e4bd008e03836
Source dataset
uspto-grants-2002_12
Patent number
US06500828B1

Reaction notes

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