1-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide → 3-(5-Methyl-pyridine-2-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 227022Notes

Reaction equation

HRID 227022 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5].[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([Mg]Br)=[N:31][CH:32]=1>O1CCCC1>[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([C:4]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:7]=2)=[O:5])=[N:31][CH:32]=1

Participants

4

Reactant 2

HCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amideHCID 178426145HCID 178426145, compound

Product 1

HCID 577546183-(5-Methyl-pyridine-2-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-oneYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 with 200 mg (0.593 mmol) of 1-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide, 5.2 mL (1.30 mmol, 0.25 M in tetrahydrofuran) of 5-methyl-2-pyridylmagnesium bromide, and 2.6 mL of tetrahydrofuran. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 77.6 mg of 3-(5-Methyl-pyridine-2-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one. LC-MSD, m/z for C23H19N3O2 [M+H]: 370.15 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 0.91 min.

Workup

  1. customThe crude product was purified by flash column chromatography
  2. customfurther purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

Sources & evidence

ORD record
ord-aeebcd86f5134a85b3e11a8261d55320
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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