Diisopropylethylamine → HCID 59242666, compound

HRID 1630458Notes

Reaction equation

HRID 1630458 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[N:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:3]=2)[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 592426496-Chloro-4-phenyl-3-(trifluoromethyl)pyridazine

Product 1

HCID 59242666HCID 59242666, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of 6-chloro-4-phenyl-3-trifluoromethyl-pyridazine (D3) (7.1 g, 0.0274 mol) and N-Boc-piperazine (5.62 g, 0.0302 mol) in acetonitrile (150 ml) was added diisopropylethylamine (5.1 ml, 0.0302 mol) and the mixture heated at 150° C. for 20 min., under microwave irradiation. After this period, the reaction mixture was diluted with dichloromethane and extracted with water. The organic layer was separated, dried (MgSO4) and the solvents evaporated in vacuo. The crude product was purified by column chromatography (silica; 20% ethyl acetate in heptane, followed by 10% ethyl acetate in dichloromethane). After evaporation of the solvent, the crude product was crystallised from heptane to yield D4 (10.4 g, 93%). C20H23F3N4O2 requires 408; Found 409 (MH+).

Workup

  1. waitAfter this period
  2. extractionextracted with water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica; 20% ethyl acetate in heptane, followed by 10% ethyl acetate in dichloromethane)
  7. customAfter evaporation of the solvent
  8. customthe crude product was crystallised from heptane

Sources & evidence

ORD record
ord-bf0795a049ec4fb7bfdb7e65a9d55a94
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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