Dimethylcarbamoyl Chloride → N'-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N,N-dimethylurea

HRID 13809

Reaction equation

HRID 13809 reaction equation
[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2].[H-].[Na+].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C1COCC1>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH:14][C:36](=[O:37])[N:35]([CH3:39])[CH3:34])=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11489632N'-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N,N-dimethylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 2 (70 mg) in THF (1 mL), under nitrogen, was cooled to 0° C. and treated with sodium hydride (60% in mineral oil) (7 mg). The suspension was stirred for 10 min were upon dimethylcarbamyl chloride (15 uL) was added. The reaction was allowed to warm to room temperature and was stirred overnight. The reaction mixture was quenched with water and extracted twice with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 50% EtOAc in hexane afforded the title compound. HPLC/MS: 543.0 (M+1), 545.0 (M+3); Rt=4.27 min.

Workup

  1. additionwas added
  2. stirringwas stirred overnight
  3. customThe reaction mixture was quenched with water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on a preparative silica TLC plate
  9. washeluted with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-7b7099260b6c452e86cd05ada177bb67
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Linked notes

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