Sodium hydride → Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

HRID 1582966Notes

Reaction equation

HRID 1582966 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([C:7]1[C:8]([NH:18][CH2:19][CH3:20])=[N:9][C:10]([CH:13]([O:16]C)OC)=[CH:11][CH:12]=1)=O.[H-].[Na+].Cl[CH:27]([CH2:33][CH2:34][C:35]([O-])=[O:36])[C:28]([O:30][CH2:31]C)=[O:29]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[N:9][C:10]([CH:13]=[O:16])=[CH:11][CH:12]=3)[N:18]([CH2:19][CH3:20])[C:35](=[O:36])[C:34]=2[CH2:33][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 227166793-(3-Chlorobenzoyl)-2-ethylamino-6-dimethoxymethylpyridineHCID 22716689Monoethyl chloroglutarate

Product 1

HCID 22716671Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF was treated 3-(3-chlorobenzoyl)-2-ethylamino-6-dimethoxymethylpyridine with 60% sodium hydride, followed by the reaction with monoethyl chloroglutarate. Thereafter, the reaction mixture was worked up and purified in a usual manner. The resulting compound was reacted in ethanol in the presence of sodium methoxide under heating, and the reaction mixture was worked up and purified in a usual manner. Then, the resulting compound was reacted in a solution of 6M hydrochloric acid-dioxane (1:1) under heating, and then the reaction mixture was worked up and purified in a usual manner. The resulting compound was further reacted with methyl iodide in DMF in the presence of potassium carbonate, and then the reaction mixture was worked up and purified in a usual manner to obtain methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate. NMR1: 10.11 (1H, d, J=0.6 Hz), 2.45-2.95 (4H, m), 1.43 (3H, t, J=7.1 Hz).

Workup

  1. custompurified in a usual manner
  2. customThe resulting compound was reacted in ethanol in the presence of sodium methoxide
  3. temperatureunder heating
  4. custompurified in a usual manner
  5. customThen, the resulting compound was reacted in a solution of 6M hydrochloric acid-dioxane (1:1)
  6. temperatureunder heating
  7. custompurified in a usual manner
  8. customThe resulting compound was further reacted with methyl iodide in DMF in the presence of potassium carbonate
  9. custompurified in a usual manner

Sources & evidence

ORD record
ord-94a99803ae264580903ddbc8215fea3b
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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