N-Methoxy-N,5-dimethylisoxazole-3-carboxamide → 3-(5-Methyl-isoxazole-3-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 227138Notes

Reaction equation

HRID 227138 reaction equation
I[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[CH:3]=1.C([Mg]Cl)(C)C.CON(C)[C:29]([C:31]1[CH:35]=[C:34]([CH3:36])[O:33][N:32]=1)=[O:30]>C1COCC1>[CH3:36][C:34]1[O:33][N:32]=[C:31]([C:29]([C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)[CH:3]=2)=[O:30])[CH:35]=1

Participants

5

Reactant 3

HCID 45099367N-Methoxy-N,5-dimethylisoxazole-3-carboxamideHCID 577545943-iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-oneHCID 178418918HCID 178418918, compound

Product 1

HCID 577545833-(5-Methyl-isoxazole-3-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-oneYield 10.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 3-Iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one (300 mg, 0.82 mmol, 1.2 eq) in THF (2 ml), was added isopropylmagnesium chloride in THF (0.88 mL, 1.76 mmol, 2.1 eq) slowly at −40° C. The reaction mixture was warmed to room temperature and stirred for 60 min, followed by the addition of 5-Methyl-isoxazole-3-carboxylic acid methoxy-methyl-amide (116 mg, 0.0.68 mmol, 1 eq). The mixture was stirred overnight, quenched with water and purified with HPLC to give the desired product (25 mg). LCMS observed for (M+H)+: 360.1.

Workup

  1. stirringThe mixture was stirred overnight
  2. customquenched with water
  3. custompurified with HPLC

Sources & evidence

ORD record
ord-c4285c470cb44e6da7d9cdb257827fa0
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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