3,3-Diphenylpropylamine → 4-[4-(3,5-Dichlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)pyridine-3-carbonyl]piperazine-1-carboxylic acid t-butyl ester

HRID 1727932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727932
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)[C:20]([C:30]([OH:32])=O)=[C:19]([CH3:33])[NH:18][C:17]=2[CH3:34])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35]1([CH:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:42][CH2:43][NH2:44])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCN=C=NCCCN(C)C.Cl.[N+]([O-])([O-])=O.[Ce+3].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>ClCCl.O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]([CH3:34])=[N:18][C:19]([CH3:33])=[C:20]([C:30](=[O:32])[NH:44][CH2:43][CH2:42][CH:41]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:21]=2[C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

8

Edukt 4

HCID 796983,3-DiphenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14029277Diammonium cerium nitrateHCID 690696744-[5-Carboxy-4-(3,5-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carbonyl]piperazine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 690707384-[4-(3,5-Dichlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)pyridine-3-carbonyl]piperazine-1-carboxylic acid t-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

300 mg (0.588 mmol) of 4-[5-carboxy-4-(3,5-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carbonyl] piperazine-1-carboxylic acid t-butyl ester, 0.12 ml (0.882 mmol) of 3,3-diphenylpropylamine and 248 mg (1.29 mmol) of WSC hydrochloride were stirred in 15 ml of dichloromethane and 1 ml of DMF at room temperature overnight. After dichloromethane was evaporated under reduced pressure, ethyl acetate was added. After being washed with saturated aqueous sodium hydrogencarbonate solution and 1 N hydrochloric acid, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in 8 ml of acetone. 811 mg (1.48 mmol) of diammonium cerium nitrate (IV) suspended in 8 ml of water was dropped and stirred at room temperature for 1 hour. After acetone was evaporated under reduced pressure, ethyl acetate was added. After being washed with water, the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 80/1) to obtain the title compound.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customAfter dichloromethane was evaporated under reduced pressure, ethyl acetate
  4. additionwas added
  5. washAfter being washed with saturated aqueous sodium hydrogencarbonate solution and 1 N hydrochloric acid
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in 8 ml of acetone
  9. additionwas dropped
  10. customAfter acetone was evaporated under reduced pressure, ethyl acetate
  11. additionwas added
  12. washAfter being washed with water
  13. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 80/1)

Quellen und Nachweise

ORD-Eintrag
ord-73f47c53d179419ab3ee47aefb82086d
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07494989B2

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