Triethylamine → HCID 25027939, compound

HRID 1864476Notes

Reaction equation

HRID 1864476 reaction equation
[CH:1]1([CH2:7][S:8]([N:11]2[CH2:15][C@@H:14]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[CH2:20][CH2:19]3)=[O:17])[NH:13][C:12]2=[O:32])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:40]1(B(O)O)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH:1]1([CH2:7][S:8]([N:11]2[CH2:15][C@@H:14]([C:16]([N:18]3[CH2:19][CH2:20][N:21]([C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[CH2:22][CH2:23]3)=[O:17])[N:13]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:12]2=[O:32])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 66827Phenylboronic Acid2×HCID 67141143HCID 67141143, compound

Product 1

HCID 25027939HCID 25027939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-cyclohexylmethanesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one (100 mg) in CH2Cl2 (3 mL) was added cupric acetate (39 mg) and triethylamine (60 μl), followed by phenyl boronic acid (53 mg). The reaction mixture was stirred at room temperature for 16 hours. Additional phenyl boronic acid (53 mg) and triethyl amine (60 μl) was added and stirring was continued for 16 hours at room temperature. The mixture was concentrated in vacuo and the residue was purified by chromatography (SiO2, n-heptane/ethyl acetate 1:1) to give (S)-1-(cyclohexylmethanesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one as a white solid. MS: 539.0 ([M+H]+)

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours at room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography (SiO2, n-heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3ea91c4e00b84b3b9104bd593b9a78cb
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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