Propargyl alcohol → HCID 21187514, compound

HRID 1383855Notes

Reaction equation

HRID 1383855 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[H-].[Na+].Cl[C:8]1[C:9]([CH:23]2[CH2:26][CH2:25][CH2:24]2)=[CH:10][C:11]2[N:12]([C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)[N:13]=1>CN(C=O)C>[CH:23]1([C:9]2[C:8]([O:4][CH2:1][C:2]#[CH:3])=[N:13][N:12]3[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:15][N:16]=[C:11]3[CH:10]=2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 21187514HCID 21187514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of propargyl alcohol (47 mg, 0.84 mmol) in DMF (2 ml) was added 60% sodium hydride suspension in oil (31 mg, 0.77 mmol). Left to stir for 5 minutes prior to the addition of 6-chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (200 mg, 0.70 mmol). Left to stir for 90 minutes. Quenched (120), extracted (ethyl acetate), washed (H2O, brine), dried (MgSO4) and evaporated in vacuo. The residue was purified via silica gel chromatography using 50/50 ethyl acetate/hexane to elute. The title compound was obtained as a white solid. 1H NMR (250 MHz, CDCl3) δ2.19-2.26 (1 H, m), 2.37-2.55 (3 H, m), 2.69-2.80 (2 H, m), 2.90 (1 H, m), 3.97 (1 H, m), 5.35 (2 H, d, J=2.4 Hz), 7.77-7.89 (3 H, m), 8.13 (1 H, s), 8.80 (1 H, s), 8.86 (1 H, s). Mass spec. ES+(M+1)=305.

Workup

  1. waitLeft
  2. waitLeft
  3. stirringto stir for 90 minutes
  4. customQuenched (120)
  5. extractionextracted (ethyl acetate)
  6. washwashed (H2O, brine)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was purified via silica gel chromatography
  10. washto elute

Sources & evidence

ORD record
ord-c3c34bf9b84d491daabea3225cd6106d
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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