m,alpha-Dichlorotoluene → 1-(3-Chloro-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

HRID 227013Notes

Reaction equation

HRID 227013 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:20])[N:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:23].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl>CN(C)C=O>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][N:11]1[C:12]2[C:17](=[N:16][C:15]([CH3:20])=[CH:14][CH:13]=2)[C:18](=[O:19])[C:9]([C:7](=[O:8])[C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH3:23])[CH:5]=2)=[CH:10]1

Participants

4

Reactant 2

HCID 12103m,alpha-DichlorotolueneHCID 577547063-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

Product 1

HCID 577545531-(3-Chloro-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-oneYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 120 mg (0.390 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 75.2 mg (0.467 mmol) of 3-chlorobenzyl chloride, 19 mg (0.467 mmol, 60% dispersion in oil), and 1 mL of N,N dimethylformamide. The solid was collected by filtration and was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane to yield 65.7 mg of 1-(3-Chloro-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C25H21ClN2O3 [M+H]: 433.12 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.5 min.

Workup

  1. filtrationThe solid was collected by filtration
  2. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-6e39a75da4c74078982107fb099ad781
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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