Triethylamine → HCID 14306449, compound

HRID 1904939Notes

Reaction equation

HRID 1904939 reaction equation
[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CCN(CC)CC.ClC(OCC)=O.[CH2:27]([O:29][C:30]([C:32]1[C:37](=[O:38])[N:36]2[CH:39]=[CH:40][CH:41]=[C:42]([SH:43])[C:35]2=[N:34][CH:33]=1)=[O:31])[CH3:28]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:27]([O:29][C:30]([C:32]1[C:37](=[O:38])[N:36]2[CH:39]=[CH:40][CH:41]=[C:42]([S:43][C:9](=[O:11])[C:8]3[CH:7]=[CH:6][C:5]([S:1](=[O:3])(=[O:4])[NH2:2])=[CH:13][CH:12]=3)[C:35]2=[N:34][CH:33]=1)=[O:31])[CH3:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8739CarzenideHCID 10928Ethyl chloroformateHCID 143064713-ethoxycarbonyl-9-mercapto-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 14306449HCID 14306449, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.48 g (2.4 mmol) of 4-sulfamoylbenzoic acid in 10 ml of DMF are added 0.29 g of Et3N and then 0.28 g ethyl chloroformate, and the mixture is stirred at room temperature for 1 hour and mixed with 0.5 g of solid 3-ethoxycarbonyl-9-mercapto-4H-pyrido[1,2-a]pyrimidin-4-one II-1. The mixture is stirred at room temperature for 2 hours, diluted with 100 ml of water and shaken with ethyl acetate. The organic layer is washed with water, dried and concentrated in vacuo. The residue is washed with ethyl acetate to give 0.68 g of the titled compound.

Workup

  1. washThe organic layer is washed with water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. washThe residue is washed with ethyl acetate

Sources & evidence

ORD record
ord-b2db750c5d8c42ae979a138e53a9491a
Source dataset
uspto-grants-1989_06
Patent number
US04840953

Reaction notes

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