Hydrochloric Acid → HCID 86596812, Verbindung

HRID 751378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751378
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[Cl:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.Cl>CO>[ClH:22].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2[NH:23][CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 13441-PyrrolidineethanamineHCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

Produkt 1

HCID 86596812HCID 86596812, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(4-tert-Butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde is reacted with 1-(2-aminoethyl)pyrrolidine as described in Step 2 of Example 29 to obtain oil. The oil is dissolved in small amount of methanol and treated with 1M ethereal hydrochloric acid. The solvents are removed and the residue is triturated with ether to yield 1-(4-tert-butylphenyl)-2-(2-pyrrolidin-1-yl-ethylamino)-1H-indole-3-carboxaldehyde hydrochloride (20% yield) as a light beige solid. ESI/MS 390 (M+H); RT 3.42 min. NMR 10.68 (1H, s); 7.95 (1H, d, J=9 Hz); 7.67 (2H, d, J=9 Hz); 7.47 (2H, d, J=9 Hz); 7.10 (2H, m); 6.63 (1H, d, J=9 Hz); 3.54 (2H, m); 3.40 (2H, m); 3.21 (2H, m); 2.83 (2H, m); 1.91 (4H, m); 1.35 (9H, s).

Aufarbeitung

  1. customto obtain oil
  2. customThe solvents are removed
  3. customthe residue is triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-c1597d408ac048a38313561210c59752
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405300B2

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