3-Phenylpropylamine → HCID 17854642, compound

HRID 1182579Notes

Reaction equation

HRID 1182579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]([OH:17])=O)=[C:13]([CH2:18][CH3:19])[N:12]=[C:11]([S:20][CH3:21])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:22]1([CH2:28][CH2:29][CH2:30][NH2:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[C:14]([C:15]([NH:31][CH2:30][CH2:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:17])=[C:13]([CH2:18][CH3:19])[N:12]=[C:11]([S:20][CH3:21])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 162593-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 17854681HCID 17854681, compound

Product 1

HCID 17854642HCID 17854642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

183 mg (0.533 mmol) of 4-(3,5-dichlorophenyl)-6-ethyl-2-(methylthio)-pyrimidine-5-carboxylic acid and 86.5 mg (0.640 mmol) of phenylpropylamine were dissolved in 10 ml of dichloromethane. 153 mg (0.800 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC hydrochloride) was added under cooling with ice and stirred at room temperature overnight. After concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate. The reaction mixture was 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 (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Workup

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

Sources & evidence

ORD record
ord-b01eaa0970f34cc5988b55e757af6526
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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