Triethylamine → N-[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]propionamide

HRID 1349504Notes

Reaction equation

HRID 1349504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:11]=[C:12]([NH2:24])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].C(N(CC)CC)C.[C:41](Cl)(=[O:44])[CH2:42][CH3:43].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:16]([O:15][C:14]1[C:13](=[O:23])[C:12]([NH:24][C:41](=[O:44])[CH2:42][CH3:43])=[CH:11][N:10]([CH2:25][CH:26]([O:27][CH3:28])[O:29][CH3:30])[C:9]=1[C:7](=[O:8])[NH:6][CH2:5][C:4]1[CH:31]=[CH:32][CH:33]=[C:2]([Cl:1])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 588591465-Amino-3-benzyloxy-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide

Product 1

HCID 21091375N-[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]propionamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-amino-3-benzyloxy-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (55 mg) in chloroform (1 ml) were added, triethylamine (0.033 ml) and propanoyl chloride (0.012 ml) at 0° C. After stirring at the same temperature for 20 min, aqueous sodium hydrogen carbonate solution was added and the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was dried, concentrated and purified by silica gel thin layer chromatography (chloroform:methanol=10:1) to give N-[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]propionamide (55 mg). By subjecting 51 mg of the obtained compound to a reaction operation similar to that in Example 187, Step 2, N-[2-(3-chlorobenzyl)-9-hydroxy-1,8-dioxo-1,8-dihydro-2H-pyrido[1,2-a]pyrazin-7-yl]propionamide (27 mg) was obtained.

Workup

  1. customat 0° C
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. custompurified by silica gel thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-7d54dcb2eb25455d924491bc2ca8abf4
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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