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1-Hydroxybenzotriazole → 4-(3-Chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-5-(3,3-diphenylpropylcarbamoyl)-2-phenyl-1,4-dihydropyrimidine

HRID 24596
Notes
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Reaction equation

HRID 24596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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)[CH:5]=[CH:6][CH:7]=1.[C:33]1([CH:39]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:40][CH2:41][NH2:42])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14](=[O:15])[NH:42][CH2:41][CH2:40][CH:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:12]([CH2:17][O:18][CH2:19][CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[NH:11][C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 757711-Hydroxybenzotriazole2×HCID 796983,3-DiphenylpropylamineHCID 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 9939371
4-(3-Chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-5-(3,3-diphenylpropylcarbamoyl)-2-phenyl-1,4-dihydropyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

60.0 mg (0.110 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid and 34.9 mg (0.165 mmol) of 3,3-diphenylpropylamine were dissolved in 10 ml of dichloromethane. 31.6 mg (0.165 mmol) of WSC hydrochloride and 16.8 mg (0.110 mmol) of 1-hydroxybenzotriazole (hereinafter referred to as “HOBT”) were added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. 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=3/1 to 1/1) to obtain the title compound.

Workup

  1. additionwere added to the obtained solution
  2. temperatureunder cooling with ice, and they
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-8b5d6045938543759c3dedfaaef04ce5
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