2-Pyridinemethanamine → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamine

HRID 81988Notes

Reaction equation

HRID 81988 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>O1CCOCC1>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole

Product 1

HCID 672076287-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamineYield 105.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitroquinoline (1.5 g, 3.5 mmol) and 2-(aminomethyl)pyridine (1.46 g, 13.5 mmol) in dioxan (10 ml) was stirred at room temperature for 2 h. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed [50-100% ethyl acetate/cyclohexane] to give the title compound as a yellow solid (1.5 g, 3.70 mmol, 82% yield). LCMS (formate) Rt 0.86 min, MH+ 406.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed [50-100% ethyl acetate/cyclohexane]

Sources & evidence

ORD record
ord-dbcb95c0d0874795a5fe863a89bf67f0
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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