1,2-Dichloroethane → (11S)-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c][1,5]naphthyridin-6-amine

HRID 221549

Reaktionsgleichung

Reaktionsgleichung von HRID 221549
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-])=O.[NH2:15][C@@H:16]([CH3:19])[CH2:17][OH:18].[F-].C([N+:25](CCCC)(CCCC)CCCC)CCC.Cl[CH2:39][CH2:40]Cl>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:19][C@@H:16]1[N:15]2[C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][N:10]=4)[N:5]=[C:4]([NH2:25])[C:3]=3[N:12]=[C:40]2[CH2:39][O:18][CH2:17]1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 80307L-AlaninolHCID 2724141Tetrabutylammonium FluorideHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Produkt 1

HCID 11514384(11S)-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c][1,5]naphthyridin-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared from 4-chloro-3-nitro[1,5]naphthyridine and (S)-(+)-2-amino-1-propanol following Parts A through G listed for the preparation of Example 1 with the modifications that in Part E the reaction with tetrabutylammonium fluoride was carried out in CH2Cl2 as the solvent, Part F was carried out in chloroform as the solvent, and Part G was carried out in 1,2-dichloroethane as the solvent. Chromatography (SiO2, 10-30% CMA/CHCl3) gave an off-white solid. Recrystallization from 1,2-dichloroethane gave (11S)-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c][1,5]naphthyridin-6-amine (0.68 g) as a white crystalline solid, mp 240-242° C.

Aufarbeitung

  1. customlisted for the preparation of Example 1 with the modifications that in Part E
  2. customRecrystallization from 1,2-dichloroethane

Quellen und Nachweise

ORD-Eintrag
ord-750416ac05b840ccba62f37867ae5612
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207162B2

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