3-Chloro-6-(trifluoromethyl)pyridazine → HCID 59320257, compound

HRID 655286Notes

Reaction equation

HRID 655286 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][C:29]([NH:31][NH2:32])=O)=[CH:23][CH:22]=3)[CH:15]=[N:14]1>C(O)CCC>[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][C:29]2[N:3]4[N:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]4=[N:32][N:31]=2)=[CH:23][CH:22]=3)[CH:15]=[N:14]1

Participants

4

Reactant 2

HCID 282425263-Chloro-6-(trifluoromethyl)pyridazineHCID 59320419HCID 59320419, compound

Product 1

HCID 59320257HCID 59320257, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-butanol (2 mL), 3-chloro-6-trifluoromethyl-pyridazine (0.13 mmol, 25 mg), [3-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-yl]-acetic acid hydrazide (0.13 mmol, 40 mg) was heated at 120° C. for 18 hours. The solvent was then removed by blowing nitrogen, the brown residue dissolved in 1 ml of dimethylformamide and one 1 ml of methanol and purified by preparatory HPLC to return the title compound (15.8 mg, 0.04 mmol, 29%). Analytical data is presented in Table 2.

Workup

  1. customThe solvent was then removed
  2. dissolutionthe brown residue dissolved in 1 ml of dimethylformamide
  3. customone 1 ml of methanol and purified by preparatory HPLC

Sources & evidence

ORD record
ord-69785ef15b68407eab1a8d6550a49f5a
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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