Trifluoromethanesulfonic anhydride → 4-Aminoquinoline

HRID 1364298

Reaktionsgleichung

Reaktionsgleichung von HRID 1364298
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.O[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.O[C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[N:26]=[CH:27][CH:28]=[N:29]2.O[C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=[CH:37][CH:36]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>P(Cl)(Cl)(Cl)=O.C1COCC1.C(Cl)Cl.ClCCCl>[NH2:14][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:26][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.[NH2:38][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[N:26]=[CH:27][CH:28]=[N:29]2.[NH2:5][C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=[CH:37][CH:36]=1

Komponenten

13

Edukt 5

HCID 67749Trifluoromethanesulfonic anhydrideHCID 1356902745-QuinoxalinolHCID 178516385quinolin-4-olHCID 178516432HCID 178516432, VerbindungHCID 178517962HCID 178517962, Verbindung

Produkt 4

HCID 684764-AminoquinolineHCID 847594-AminoquinazolineHCID 854945-AminoquinoxalineHCID 5893541,5-Naphthyridin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

To prepare the compound I-1, a 4-hydroxy-[1,5]-naphthyridine, a 4-hydroxyquinazoline, a 5-hydroxyquinoxaline or a 4-hydroxyquinoline derivative can be converted into the corresponding chloro derivative by heating in phosphorous oxychloride between 40° C. and 100° C. neat or in an inert solvent like 1,2-DCE, or to the corresponding trifluoromethanesulphonyloxy derivative by reaction with trifluoromethanesulphonic anhydride, in the presence of an organic base between −40° C. and 80° C. in an aprotic solvent like DCM or THF (K. Ritter, Synthesis (1993), 735). The corresponding 4-amino-[1,5]-naphthyridine, 4-aminoquinazoline, 5-aminoquinoxaline or 4-aminoquinoline derivatives can then be obtained by reaction of the corresponding trifluoromethanesulphonyloxy derivatives with ammonia in a solvent like DCM or THF, or with n-propylamine hydrochloride in pyridine between −20° C. and 100° C. (R. Radinov, Synthesis (1986), 886). The corresponding 4-aminoquinazoline can also be obtained from its 4-chloro analogue by reaction with ammonia under the same conditions.

Aufarbeitung

  1. customTo prepare the compound I-1
  2. customin the presence of an organic base between −40° C. and 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-f62cbbdfca50487cab13e63d926d80a9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888359B2

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