Sodium hydride → HCID 22457796, compound

HRID 1383851Notes

Reaction equation

HRID 1383851 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Na+].Cl[C:13]1[C:14]([C:28]2([CH3:33])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:15][C:16]2[N:17]([C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20][N:21]=2)[N:18]=1>CN(C)C=O>[CH3:33][C:28]1([C:14]2[C:13]([O:1][CH2:2][C:3]3[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=3)=[N:18][N:17]3[C:19]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[N:20][N:21]=[C:16]3[CH:15]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1514369(3-Methylpyridin-2-yl)methanolHCID 21187534HCID 21187534, compound

Product 1

HCID 22457796HCID 22457796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxymethyl-3-methylpyridine (43 mg) was dissolved in dimethylformamide (2 ml) under N2. Sodium hydride (60% w/w in oil, 14 mg) was added followed after 5-10 minutes by 6-chloro-7-(1-methylcyclopentyl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (100 mg). Reaction was stirred at room temperature for 18 hours, partitioned between ethyl acetate and water, organic phase separated, dried (MgSO4) and evaporated to dryness. Recrystled from ethyl acetate to give pure product. 1H NMR (360 MHz, CDCl3) δ1.30 (3 H, s), 1.77 (6 H, m), 1.93 (2 H, m), 2.44 (3 H, s), 5.62 (2 H, s), 7.25 (1 H, m), 7.50 (3 H, m), 7.58 (1 H, d, J=7.8 Hz), 7.92 (1 H, s), 8.42 (2 H, d, J=6.4 Hz), 8.50 (1 H, m), ms (ES+) m/e 400 [MH]+.

Workup

  1. customReaction
  2. custompartitioned between ethyl acetate and water, organic phase
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customto give pure product

Sources & evidence

ORD record
ord-d9e493ff33894dfd9da41282caf05673
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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