HCID 58072196, compound → HCID 58072182, compound

HRID 1805481Notes

Reaction equation

HRID 1805481 reaction equation
CON(C)[C:4]([C:6]1[C:11](=[O:12])[CH:10]=[CH:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:7]=1)=[O:5].[CH3:24][CH2:25][Mg+].[Br-]>C1COCC1>[C:4]([C:6]1[C:11](=[O:12])[CH:10]=[CH:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[N:7]=1)(=[O:5])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 58072196HCID 58072196, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 58072182HCID 58072182, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-methoxy-N-methyl-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (1.20 g, 3.52 mmol) in THF (20 mL) was added EtMgBr (1.0 M in THF, 7.04 mL, 7.04 mmol) at −78° C. under N2. The mixture was stirred at −78° C. for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution at −78° C. The mixture was warmed to room temperature, extracted with EtOAc, dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100) to yield the title compound (767 mg, 74% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 1.06 (3H, t, J=7.2 Hz), 2.99 (2H, q, J=7.2 Hz), 6.73 (1H, d, J=8.3 Hz), 7.79-7.88 (2H, m), 8.06-8.17 (2H, m), 8.97 (1H, d, J=8.3 Hz).

Workup

  1. customThe reaction was quenched with saturated NH4Cl aqueous solution at −78° C
  2. temperatureThe mixture was warmed to room temperature
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100)

Sources & evidence

ORD record
ord-37e1e6d522464bbc90ab77fdf860f5ff
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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