3-Phenylprop-2-en-1-amine → HCID 69747300, compound

HRID 24597Notes

Reaction equation

HRID 24597 reaction equation
ClC1C=C([CH:8]2[C:13]([C:14](O)=[O:15])=[C:12]([CH2:17][O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[NH:11][C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:9]2)C=CC=1.[CH2:33]([NH2:42])[CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CCN=C=NCCCN(C)C.[ClH:54].[CH:55]1[CH:56]=[CH:57][C:58]2N(O)N=N[C:59]=2[CH:60]=1>ClCCl>[Cl:54][C:55]1[CH:60]=[C:59]([CH:8]2[C:13]([C:14](=[O:15])[NH:42][CH2:33][CH:34]=[CH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:12]([CH2:17][O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[NH:11][C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:9]2)[CH:58]=[CH:57][CH:56]=1

Participants

6

Reactant 4

HCID 203693-Phenylprop-2-en-1-amineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 155461044-(3-Chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid

Product 1

HCID 69747300HCID 69747300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

110 mg (0.243 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid and 38.8 mg (0.292 mmol) of cinnamylamine were dissolved in 10 ml of dichloromethane. 69.9 mg (0.365 mmol) of WSC hydrochloride and 37.2 mg (0.243 mmol) of HOBT were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and then washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium 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. temperatureunder cooling with ice, and they
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-71961f7b1cb146d0b98cdf5f2a52f167
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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