Water → HCID 9886575, compound

HRID 429745Notes

Reaction equation

HRID 429745 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([CH2:9][OH:10])=[N:7][CH:6]=[N:5]1.Cl[C:12]1[C:13]([N:27]2[CH2:32][CH:31]=[CH:30][CH2:29][CH2:28]2)=[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.O>CN(C=O)C>[N:27]1([C:13]2[C:12]([O:10][CH2:9][C:8]3[N:4]([CH3:3])[N:5]=[CH:6][N:7]=3)=[N:17][N:16]3[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:19][N:20]=[C:15]3[CH:14]=2)[CH2:28][CH:29]=[CH:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 18353334HCID 18353334, compound

Product 1

HCID 9886575HCID 9886575, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 23 mg, 0.58 mmol) was added to a solution of (2-methyl-2H-1,2,4-triazol-3-yl)methanol (EP-A-421210) (57 mg, 0.53 mmol) in dry DMF (2 ml) at room temperature under nitrogen. After 1 hour at room temperature a solution of 6-chloro-7-(3,6-dihydro-2H-pyridin-1-yl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (150 mg) in dry DMF (2 ml) was added via syringe. The mixture was stirred at room temperature for 16 hours. Water (20 ml) was added and the solid filtered and dried in vacuo. Recrystallisation from ethyl acetate/petroleum ether afforded the title pyridaziite as a white solid (131 mg, 70%). 1H NMR (250 MHz, CDCl3) 8.29 (2H, m), 7.94 (1H, s), 7.52 (3H, m), 7.23 (1H, s), 5.91 (1H, m), 5.80 (1H, m), 5.63 (2H, s), 3.96 (3H, s), 3.71 (2H, m), 3.40 (2H, m), 2.23 (2H, m). MS (ES+) 389 [MH]+.

Workup

  1. filtrationthe solid filtered
  2. customdried in vacuo
  3. customRecrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-d4b8cf8b230542eda1a10f113f957553
Source dataset
uspto-grants-2001_11
Patent number
US06319924B1

Reaction notes

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