Hydrochloric Acid → HCID 11339067, Verbindung

HRID 1765552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765552
Cl.Cl.CCOCC.Cl.Cl.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][N:23]([CH2:38][CH2:39][CH3:40])[CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][N:23]([CH2:38][CH2:39][CH3:40])[CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 10953452Ether hydrochlorideHCID 69497606HCID 69497606, Verbindung

Produkt 1

HCID 11339067HCID 11339067, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To N-[3-(5-fluoro-1H-indol-3-yl)propyl]-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine (example 21) (0.13 g, 0.34 mmol) in anhydrous methanol (20 mL), was added propionaldehyde (0.25 mL, 3.4 mmol), acetic acid (0.2 ml, 0.34 mmol) and sodium cyanoborohydride (0.041 g, 0.65 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 1N NaOH, and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography (5% MeOH/CH2Cl2) afforded 0.11 g (77%) of product as a clear oil. It was converted to the HCl salt by dissolution in ethyl acetate and addition of 1M HCl/Et2O (2.4 eq) to generate N-[3-(5-fluoro-1H-indol-3-yl)propyl]-N-propyl-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a light yellow solid: mp>148° C. MS ESI m/z 416 [M−H]−. Elemental Analysis for C26H28FN3O·2.00 HCl; Calculated: C, 63.67; H, 6.17; N, 8.57. Found: C, 63.97; H, 6.48; N, 8.28.

Quellen und Nachweise

ORD-Eintrag
ord-cedc0cb91e5b44a29f3a0cb7ba7a0f3a
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07227023B2

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