3-Phenylpropylamine → 4-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramide

HRID 389976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389976
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N([CH:32]([CH3:34])[CH3:33])CC)(C)C.O.[OH:36]N1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[C:58]1([CH2:64]CCN)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:58]1([CH2:64][CH2:34][CH2:32][C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]3)=[CH:6][N:7]=2)=[O:36])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Komponenten

9

Edukt 5

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67419145[4-(6-Aminopyridin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

Produkt 1

HCID 111911704-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramideAusbeute 12,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in dichloromethane was added diisopropylethylamine (0.084 mL, 0.48 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.018 g, 0.12 mmol), EDCl (0.023 g, 0.12 mmol) and DMAP (0.015 g, 0.12 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.020 g, 0.12 mmol) was added. After stirring for 18 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a pale white solid (6.2 mg, 12.5% yield). 1H NMR (300 MHz, CDCl3) δ 8.12, 7.97, 7.87, 7.72, 7.59, 7.34, 7.10-7.29, 3.98, 3.34, 3.22, 3.02, 2.70, 2.37, 2.08. MS (ES+) m/z 497.2 (M+1).

Aufarbeitung

  1. stirringAfter stirring for 18 h
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0eb8be18f1c644dd936b3733eba66ee7
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383628B2

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