Methylamine → 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine

HRID 45864Notes

Reaction equation

HRID 45864 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)=[N:10][N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:31][NH2:32]>O.O1CCOCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:11]2[CH:12]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:32][CH3:31])[CH:7]=3)[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)=[N:10]2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 671840032-fluoro-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine

Product 1

HCID 671843124-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amineYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

500 mg (1.24 mmol) of 2-fluoro-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine were dissolved in a mixture of 6 ml of methylamine 40% in water and 12 ml of dioxane and the mixture submitted to microwave irradiation at 130° C. for 2 hours in a sealed vial. The solvent was the removed under reduced pressure and the residue taken up with dichloromethane and washed with water. The organic layer was dried over sodium sulphate and evaporated. The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 9/1), giving 300 mg (58%) of the title compound.

Workup

  1. customirradiation at 130° C. for 2 hours in a sealed vial
  2. customremoved under reduced pressure
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated
  6. customThe crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 9/1)

Sources & evidence

ORD record
ord-08eb875df03f4c1fb173c0d68de965e0
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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