1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl [[4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl]-(3-phenyl-2-propene-1-yl)-amino]acetate

HRID 24620Notes

Reaction equation

HRID 24620 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[NH:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:19]1([CH:25]=[CH:26][CH2:27][NH:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([N:28]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH:26]=[CH:25][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:12]([CH3:17])[NH:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225701824-(3-Chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acidHCID 73192259Methyl (3-phenyl-2-propene-1-ylamino)acetate

Product 1

HCID 73704953Methyl [[4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl]-(3-phenyl-2-propene-1-yl)-amino]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

320 mg (1.20 mmol) of 4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid was dissolved in 2 ml of DMF. 280 mg (1.20 mmol) of methyl (3-phenyl-2-propene-1-ylamino)acetate and 276 mg (1.44 mmol) of WSC hydrochloride were added to the obtained solution, and they were stirred at room temperature overnight. After the extraction with ethyl acetate, the extract was dried over magnesium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (methylene chloride/methanol=200/1 to 50/1) to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. dry with materialthe extract was dried over magnesium sulfate
  3. customEthyl acetate was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (methylene chloride/methanol=200/1 to 50/1)

Sources & evidence

ORD record
ord-340f1e4a03784978b9a0f3a072be0463
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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