Hydrochloric Acid → HCID 59242668, compound

HRID 1485868Notes

Reaction equation

HRID 1485868 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.[CH2:18]1[NH:23][CH2:22][CH2:21][N:20]2[CH2:24][CH2:25][CH2:26][CH:19]12.C(N(C(C)C)CC)(C)C.Cl>C(#N)C.ClCCl.C(OCC)C>[C:12]1([C:4]2[CH:3]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]4[CH2:24][CH2:25][CH2:26][CH:19]4[CH2:18]3)[N:7]=[N:6][C:5]=2[C:8]([F:11])([F:10])[F:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 592426496-Chloro-4-phenyl-3-(trifluoromethyl)pyridazine

Product 1

HCID 59242668HCID 59242668, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-chloro-4-phenyl-3-trifluoromethyl-pyridazine (D3) (0.10 g, 0.39 mmol), octahydro-pyrrolo(1,2-a)pyrazine, racemic mixture, (0.053 g, 0.42 mmol) and diisopropylethylamine (0.103 ml, 0.585 mmol) in acetonitrile (3 ml) was stirred at 150° C. for 30 min., under microwave irradiation. The reaction mixture was then diluted with dichloromethane (25 ml) and extracted with a saturated solution of sodium carbonate (12 ml). The organic layers were separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was then purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The residue was precipitated from acetonitrile/heptane. The product obtained was treated with a solution of hydrochloric acid in diethyl ether (2M) to yield the corresponding salt E5 (0.081 g, 54%) as a white solid. C18H19F3N4.HCl; free base requires 348; Found 349 (MH+).

Workup

  1. extractionextracted with a saturated solution of sodium carbonate (12 ml)
  2. customThe organic layers were separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was then purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7M)/dichloromethane)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. customThe residue was precipitated from acetonitrile/heptane
  10. customThe product obtained

Sources & evidence

ORD record
ord-9618fa31e5a94be6871458bec775c55b
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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