N-Methylbenzylamine → HCID 21934275, compound

HRID 891349Notes

Reaction equation

HRID 891349 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li]CCCC.[Cl:15][C:16]1[CH:17]=[C:18]([N:22]2[C:27](=[O:28])[C:26](OC)=[C:25]([C:31]3[CH:36]=[CH:35][C:34]([S:37][CH3:38])=[CH:33][CH:32]=3)[CH:24]=[N:23]2)[CH:19]=[CH:20][CH:21]=1>O1CCCC1>[Cl:15][C:16]1[CH:17]=[C:18]([N:22]2[C:27](=[O:28])[C:26]([N:2]([CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH3:1])=[C:25]([C:31]3[CH:36]=[CH:35][C:34]([S:37][CH3:38])=[CH:33][CH:32]=3)[CH:24]=[N:23]2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 21934294HCID 21934294, compoundHCID 178418339Butyllithium

Product 1

HCID 21934275HCID 21934275, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

To a rapidly stirred 0° C. mixture of N-methylbenzylamine (67.5 mg, 0.56 mmol) and tetrahydrofuran (3.7 mL) was slowly added dropwise an n-BuLi solution (0.235 mL, 0.59 mmol, 2.5 M in hexanes). The reaction mixture was stirred for 10 minutes at 0° C. and 1 hour at 23° C. The solution was cooled to −78° C., and a tetrahydrofuran (10-15 mL) solution of the 2-(3-chlorophenyl)-4-methoxy-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone (200 mg, 0.56 mmol) slowly added along the interior wall of the reaction vessel. This reaction mixture was stirred overnight, slowly warming to 23° C. as the cooling bath evaporated. The reaction was quenched with water and diluted with a large excess of ethyl acetate. The layers were separated, and the ethyl acetate layer washed with additional water and brine and dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (flash silica gel, ethyl acetate/hexanes 1:9) to provide 2-(3-chlorophenyl)-4-(N-methyl benzylamino)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone (yield: 145 mg, 58%).

Workup

  1. temperatureThe solution was cooled to −78° C.
  2. stirringThis reaction mixture was stirred overnight
  3. temperatureslowly warming to 23° C. as the cooling bath
  4. customevaporated
  5. customThe reaction was quenched with water
  6. additiondiluted with a large excess of ethyl acetate
  7. customThe layers were separated
  8. washthe ethyl acetate layer washed with additional water and brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was chromatographed (flash silica gel, ethyl acetate/hexanes 1:9)

Sources & evidence

ORD record
ord-76b662433d55429397e69d633bdd2b9a
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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