6-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine → HCID 67339893, compound

HRID 1674972Notes

Reaction equation

HRID 1674972 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:20]([O:24][C:25](=[O:35])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=1)([CH3:23])([CH3:22])[CH3:21]>C(O)(=O)C.ClCCl>[F:19][C:16]([F:17])([F:18])[C:13]1[N:11]2[N:12]=[C:7]([N:1]3[CH2:2][CH2:3][N:4]([CH2:33][C:30]4[CH:29]=[CH:28][C:27]([NH:26][C:25](=[O:35])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:32][CH:31]=4)[CH2:5][CH2:6]3)[CH:8]=[CH:9][C:10]2=[N:15][N:14]=1

Participants

5

Reactant 2

HCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineHCID 2771821tert-Butyl (4-formylphenyl)carbamate

Product 1

HCID 67339893HCID 67339893, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.079 g, 0.29 mmol) in a mixture of acetic acid and dichloromethane (1:9; 3 mL) was added to a mixture of (polystyrylmethyl)trimethylammonium cyanoborohydride (4.1 mmol/g, 0.097 g, 0.4 mmol) and N-(4-formylphenyl)carbamic acid tert-butyl ester (0.088.4 g, 0.4 mmol). The reaction mixture was shaken for 4 days and then filtered. The filtrate was evaporated and the and the involatile residue was purified by hplc using a Waters XBridge Prep C18 OBD column (5μ silica, 21 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of water (containing 0.05% aqueous ammonia) and acetonitrile as eluents to give tert-butyl 4-((4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazin-1-yl)methyl)phenylcarbamate (0.0722 g, 52%) as a white solid, which was used without further purification.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe and the involatile residue was purified by hplc
  4. washeluted with decreasingly polar mixtures of water (containing 0.05% aqueous ammonia) and acetonitrile as eluents

Sources & evidence

ORD record
ord-01f5edeb81124dbfb88d2d21785dcee1
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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