Potassium Iodide → HCID 59805854, compound

HRID 1429657Notes

Reaction equation

HRID 1429657 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.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[I-].[K+]>O>[F:9][C:8]([F:11])([F:10])[C:5]1[N:4]=[N:3][C:2]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 12682914-Amino-1-Boc-piperidineHCID 282425263-Chloro-6-(trifluoromethyl)pyridazine

Product 1

HCID 59805854HCID 59805854, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-chloro-6-trifluoromethyl-pyridazine (4.4 g, 24.1 mmol) (prepared by a procedure similar to that described in Tetrahedron, 1999, 55 (52), 15067-15070), 4-amino-1-tert-butyloxycarbonylpiperidine (9.63 g, 48.1 mmol) and potassium iodide (cat.) were heated in a melt at 150° C. for 30 min. After this period, the reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was separated, dried and the solvent evaporated in vacuo. The crude product was purified by chromatography (silica; 1%-4% ammonia in methanol (7 M)/dichloromethane) to give D1 (7.06 g, 85%). C15H21F3N4O2 requires 346; Found 347 (MH+)

Workup

  1. customprepared by a procedure similar to
  2. waitAfter this period
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. customdried
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by chromatography (silica; 1%-4% ammonia in methanol (7 M)/dichloromethane)

Sources & evidence

ORD record
ord-71b79922ffd1499da15b5f34a39a8db3
Source dataset
uspto-grants-2015_01
Patent number
US08940743B2

Reaction notes

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