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3,3-Diphenylpropylamine → 3-Carbamoyl-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

HRID 24615
Notes
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Reaction equation

HRID 24615 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C:8]([C:17]([OH:19])=O)=[C:7]([CH3:20])[NH:6][C:5]1=[O:21])(=[O:3])[NH2:2].[C:22]1([CH:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][CH2:30][NH2:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[C:32]1([CH:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:29][CH2:30][NH:31][C:17]([C:8]2[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=3)[N:4]([C:1](=[O:3])[NH2:2])[C:5](=[O:21])[NH:6][C:7]=2[CH3:20])=[O:19])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 796983,3-DiphenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225702053-Carbamoyl-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Product 1

HCID 207589143-Carbamoyl-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

102 mg (0.329 mmol) of 3-carbamoyl-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 83.5 mg (0.395 mmol) of (3,3-diphenylpropyl)amine were dissolved in 10 ml of DMF. 94.6 mg (0.494 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 basic silica gel chromatography (dichloromethane/methanol=100/1 to 10/1) to obtain the crude 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 basic silica gel chromatography (dichloromethane/methanol=100/1 to 10/1)

Sources & evidence

ORD record
ord-7dec7d03f2974fa1bdcd7c1807e14982
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855716B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes