Diisopropylethylamine → tert-Butyl 4-[6-(trifluoromethyl)pyridazin-3-yl]piperazine-1-carboxylate

HRID 1630463Notes

Reaction equation

HRID 1630463 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(N(C(C)C)CC)(C)C>C(#N)C>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[N:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 282425263-Chloro-6-(trifluoromethyl)pyridazine

Product 1

HCID 53485513tert-Butyl 4-[6-(trifluoromethyl)pyridazin-3-yl]piperazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-3-trifluoromethylpyridazine (0.666 g, 5.09 mmol) (prepared by following the procedure described in Goodman, A. J.; Stanforth, S. P; Tarbit B. Tetrahedron 1999, 55, 15067-15070), N-Boc-piperazine (1.138 g, 6.11 mmol) and diisopropylethylamine (1.95 ml, 1.12 mmol) in acetonitrile (10 ml) was stirred at 180° C. for 30 min., under microwave irradiation. The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica gel; hexane/ethyl acetate) to yield D9 (1.67 g, 99%) as a light yellow solid. C14H19F3N4O2 requires 332; Found 333 (MH+).

Workup

  1. customprepared
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by column chromatography (silica gel; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-70371dca357d49fe9abf6cfc6bd6f45a
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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