1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(4-(pyridin-3-ylmethyl)piperazine-1-carbonyl)piperidin-1-yl)methanone

HRID 83620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83620
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH2:56][N:57]2[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]2)[CH:51]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]([N:60]3[CH2:61][CH2:62][N:57]([CH2:56][C:52]4[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=4)[CH2:58][CH2:59]3)=[O:25])[CH2:22][CH2:23]2)=[O:17])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1569751-[(Pyridin-3-yl)methyl]piperazineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 66571214(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(4-(pyridin-3-ylmethyl)piperazine-1-carbonyl)piperidin-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-hydroxybenzotriazole (68.1 mg, 0.504 mmol) and EDCI (97 mg, 0.504 mmol) were dissolved in DCM (Volume: 4.0 ml). The suspension was stirred at room temperature for 10 minutes where it turned clear. Hunig'sBase (0.088 ml, 0.504 mmol) and 1-(pyridin-3-ylmethyl)piperazine (100 mg, 0.564 mmol) were added. The reaction was stirred at room temperature overnight. It was diluted with water and ethyl acetate. The water layer was washed with another portion of ethyl acetate. The combined organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The dark brown oil crude material was purified using 5% Methanolic ammonia/DCM resulting in a white solid as a product. (Yield: 105 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.51-8.45, 7.74-7.68, 7.62, 7.53, 7.39-7.30, 7.24-7.18, 7.13-7.07, 6.73, 5.49, 4.58-3.85, 3.55-3.42, 3.13-2.80, 2.40-2.27, 1.60, 1.36

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature overnight
  2. washThe water layer was washed with another portion of ethyl acetate
  3. washThe combined organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe dark brown oil crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-b20686dfc3e54e77998133dd4b10b49e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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