N'-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)propanehydrazide → 6-(1-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl)quinoline

HRID 219187Notes

Reaction equation

HRID 219187 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:10](=O)[CH:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH3:12])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[CH3:12])=[N:9][N:8]=2)[N:7]=1

Participants

3

Reactant 1

HCID 57691205N'-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)propanehydrazide

Product 1

HCID 249687116-(1-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl)quinoline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N′-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)propanehydrazide (4300 mg, 13119 μmol) in TFA (40 mL) was heated to 120° C. with microwaves for 40 min. LCMS suggests very good converson. Solvents removed under reduced pressure and residue partitioned between 9:1 CHCl3/IPA (75 mL) and 1M NaOH (100 mL). Aqueous further extracted with 9:1 CHCl3/IPA (2×25 mL). Combined organics dried over MgSO4, concentrated, and oily residue dissolved in ACN/MeOH (2 mL). Resulting solid after 2 h was isolated by filtration and washed with ACN (5 mL). 6-(1-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl)quinoline isolated as a white solid. MS (ESI pos. ion) m/z: 310 (MH+). Calc'd exact mass for C16H12ClN5: 309.

Workup

  1. customSolvents removed under reduced pressure and residue
  2. custompartitioned between 9:1 CHCl3/IPA (75 mL) and 1M NaOH (100 mL)
  3. extractionAqueous further extracted with 9:1 CHCl3/IPA (2×25 mL)
  4. dry with materialCombined organics dried over MgSO4
  5. concentrationconcentrated
  6. dissolutionoily residue dissolved in ACN/MeOH (2 mL)
  7. customResulting solid after 2 h
  8. customwas isolated by filtration
  9. washwashed with ACN (5 mL)

Sources & evidence

ORD record
ord-49ad2674ce6c4b0898339c035292e8cd
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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