Hydrochloric Acid → HCID 59242660, compound

HRID 1485867Notes

Reaction equation

HRID 1485867 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.[CH3:18][C@H:19]1[CH2:24][NH:23][CH2:22][C@@H:21]([CH3:25])[NH:20]1.C(N(C(C)C)CC)(C)C.Cl>C(#N)C.C(OCC)C>[CH3:18][C@H:19]1[NH:20][C@@H:21]([CH3:25])[CH2:22][N:23]([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)[CH2:24]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 592426496-Chloro-4-phenyl-3-(trifluoromethyl)pyridazine

Product 1

HCID 59242660HCID 59242660, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-chloro-4-phenyl-3-trifluoromethyl-pyridazine (D3) (0.15 g, 0.58 mmol), 2,6-cis-dimethylpiperazine (0.097 g, 0.87 mmol) and diisopropylethylamine (0.202 ml, 1.16 mmol) in acetonitrile (3 ml) was stirred at 180° C. for 30 min., under microwave irradiation. The solvent was evaporated in vacuo and then dichloromethane and a saturated solution of ammonium chloride were added. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica gel; 1-3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The product thus obtained was treated with a solution of hydrochloric acid in diethyl ether (2M) to yield the corresponding salt E4 (0.058 g, 27%; CIS) as a pale brown solid. C17H19F3N4.HCl; free base requires 336. Found 337 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additiondichloromethane and a saturated solution of ammonium chloride were added
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; 1-3% ammonia in methanol (7M)/dichloromethane)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo
  8. customThe product thus obtained

Sources & evidence

ORD record
ord-3f70ed9320164b418cad20cdfb7b0918
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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