Sodium hydride → HCID 54398397, compound

HRID 1383839Notes

Reaction equation

HRID 1383839 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[N:5][CH:4]=[N:3]1.[H-].[Na+].Cl[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][N:20]=2)[N:17]=1>CN(C=O)C.O>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:19][N:20]=3)[N:17]=2)=[N:5][CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 9114626-Chloro-3-phenyl[1,2,4]triazolo[4,3-b]pyridazineHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 54398397HCID 54398397, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2-methyl-2 H-1,2,4-triazol-3-yl)methanol (0.9 g, 8.0 mmol) (prepared using the conditions described in EP-A-421210) in DMF (30 ml) was added sodium hydride (0.32 g of a 60% dispersion in oil, 1.6 mol eq.) and the reaction mixture was stirred at room temperature for 30 minutes. After this time the product from Example 88 Step a) (1.15 g, 5.0 mmol) was added as a solution in DMF (20 ml) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water (200 ml) and the aqueous extracted with dichloromethane (4×150 ml). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel using 4% MeOH in dichloromethane as eluent to give the required product, (1.5 g, mp=254° C.). 1H NMR (360 MHz, CDCl3) δ3.98 (3 H, s), 5.61 (2 H, s), 6.90 (1 H, d, J=9.8 Hz), 7.51-7.60 (3 H, m), 7.94(1 H, s), 8.12 (1 H, d, J=9.8 Hz), 8.39 (2 H, dd, J=9.6, 1.5 Hz); MS (ES+) m/e 308 [MH]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. extractionthe aqueous extracted with dichloromethane (4×150 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel using 4% MeOH in dichloromethane as eluent

Sources & evidence

ORD record
ord-fe4fb98af2704abe9c566f21a437cb8f
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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