4-Cyanobenzoyl chloride → Lecozotan

HRID 1794990

Reaktionsgleichung

Reaktionsgleichung von HRID 1794990
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([C@H:17]([CH3:26])[CH2:18][NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)#[N:28]>ClCCl>[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:19]([CH2:18][C@H:17]([N:14]2[CH2:15][CH2:16][N:11]([C:10]3[C:5]4[O:4][CH2:3][CH2:2][O:1][C:6]=4[CH:7]=[CH:8][CH:9]=3)[CH2:12][CH2:13]2)[CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[O:34])=[CH:31][CH:30]=1)#[N:28]

Komponenten

4

Edukt 2

HCID 801724-Cyanobenzoyl chlorideHCID 11279673{(R)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}-pyridin-2-ylamine

Produkt 1

HCID 10116877Lecozotan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of {(R)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}-pyridin-2-ylamine (0.846 g, 2.38 mmol) in dichloromethane (20 mL) was treated at 0° C. with the dropwise addition of a dichloromethane solution of 4-cyanobenzoyl chloride (1.1 equivalents, 2.63 mmol in 5 mL). After stirring for 16 hours the mixture was poured onto hexane (100 mL) to precipitate the titled compound as its mono-hydrochloride salt (white solid, 1.2 g, 97% yield), which was recrystallized from dichloromethane/hexane.

Aufarbeitung

  1. additionwas poured onto hexane (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-44c6f90b057242d9ac59ef30871b3f87
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026320B2

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