Triethylamine → N-[6-(2-Chlorophenyl)-1-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridin-3-yl]-4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidine-1-carboxamide

HRID 1671611Notes

Reaction equation

HRID 1671611 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:10](=[O:26])[N:11]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[CH:13][CH:14]=1.Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].[Cl-].[O:41]=[C:42]1[NH:46][C:45]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:44][N:43]1[CH:53]1[CH2:58][CH2:57][NH2+:56][CH2:55][CH2:54]1>O1CCCC1>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[N:11]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:10](=[O:26])[C:9]([NH:8][C:28]([N:56]2[CH2:57][CH2:58][CH:53]([N:43]3[CH:44]=[C:45]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[NH:46][C:42]3=[O:41])[CH2:54][CH2:55]2)=[O:29])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 673433224-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidinium chlorideHCID 67344370amino-6-(2-chlorophenyl)-1-(cyclopropylmethyl)pyridin-2(1H)one

Product 1

HCID 59825898N-[6-(2-Chlorophenyl)-1-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridin-3-yl]-4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidine-1-carboxamideYield 14.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (9 μL, 0.062 mmol) was added to a solution of amino-6-(2-chlorophenyl)-1-(cyclopropylmethyl)pyridin-2(1H)one (17 mg, 0.062 mmol) and 4-nitrophenyl chloroformate (13 mg, 0.062 mmol) in tetrahydrofuran (2 mL) at 0° C. After 0.5 h, 4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidinium chloride (20 mg, 0.071 mmol) and triethylamine (0.030 mL, 0.215 mmol) were added and the mixture allowed to warm to ambient temperature. After 2 h, the mixture was concentrated in vacuo. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) followed by reverse phase HPLC(C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (5 mg). MS 544.2 (M+1).

Workup

  1. waitAfter 2 h
  2. concentrationthe mixture was concentrated in vacuo
  3. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-4e4cad4eb32b4b759439294e9f597ecf
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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