Piconol → HCID 22457778, compound

HRID 1383841Notes

Reaction equation

HRID 1383841 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Na+].Cl[C:12]1[C:13]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:14][C:15]2[N:16]([C:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[N:19][N:20]=2)[N:17]=1>CN(C)C=O>[CH:26]1([C:13]2[C:12]([O:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)=[N:17][N:16]3[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[N:19][N:20]=[C:15]3[CH:14]=2)[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 21187512HCID 21187512, compound

Product 1

HCID 22457778HCID 22457778, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

b 2-Hydroxymethylpyridine (56 mg) was dissolved in dimethylformamide (2 ml) under N2. Sodium hydride (60% w/w in oil, 21 mg) was added followed after 5-10 minutes by 6-chloro-7-cyclopentyl-3-(thiophen-2-yl)-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. Recrystallized in ethyl acetate in ether or methanol to give pure product. 1H NMR (250 MHz, CDCl3) δ1.73 (6 H, m), 2.16 (2 H, m) 3.38 (1 H, m), 5.68 (2 H, s), 7.21 (1 H, m), 7.28 (1 H, m), 7.51 (2 H, m), 7.77 (1 H, m), 7.88 (1 H, d, J=1.1 Hz), 8.15 (1 H, m), 8.65 (1 H, m); MS (ES+) m/e 377 [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. customRecrystallized in ethyl acetate in ether
  7. custommethanol to give pure product

Sources & evidence

ORD record
ord-0ab7a84498094e7f95a1764721333b06
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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