3-Phenylpropylamine → 4-(3-Chlorophenyl)-6-methoxymethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide

HRID 24601

Reaction equation

HRID 24601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([OH:16])=O)=[C:12]([CH2:17][O:18][CH3:19])[NH:11][C:10](=[O:20])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:21]1([CH2:27][CH2:28][CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl>ClCCl>[C:21]1([CH2:27][CH2:28][CH2:29][NH:30][C:14]([C:13]2[CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:9][C:10](=[O:20])[NH:11][C:12]=2[CH2:17][O:18][CH3:19])=[O:16])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 162593-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225701464-(3-Chlorophenyl)-6-methoxymethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Product 1

HCID 207588964-(3-Chlorophenyl)-6-methoxymethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60.0 mg (0.225 mmol) of 4-(3-chlorophenyl)-6-methoxymethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 36.5 mg (0.270 mmol) of 3-phenylpropylamine were dissolved in 10 ml of dichloromethane. 64.7 mg (0.338 mmol) of WSC hydrochloride was added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 10/1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. concentrationAfter the concentration under reduced pressure
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 10/1)

Sources & evidence

ORD record
ord-1217d5ceef1445f994aafb55c5c4d737
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Linked notes

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