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

HRID 227074Notes

Reaction equation

HRID 227074 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]>C1COCC1.[Br-]>[CH3:7][N:8]([CH3:17])[C:9]1[CH:14]=[CH:13][C:12]([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])=[CH:11][CH:10]=1

Participants

4

Reactant 1

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

Product 1

HCID 577547133-(4-Dimethylamino-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 2

HCID 259Bromide ionSolventHCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 138 mg (0.41 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2 mL THF and 2 mL 0.5M 4-N,N-dimethylanilinemagnesium bromide. Yield: 17 mg of a white solid. LC-MSD, m/z for C25H23N3O2 [M+H]+=398.1; HPLC retention time: 1.9 min.

Sources & evidence

ORD record
ord-1e4db1be7c4f440ebbb135e865d1da2f
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…