2,6-Dichloro-4-(trifluoromethyl)pyridin-3-amine → (4aS,9bR)-8-(2,6-dichloro-4-trifluoromethyl-pyridin-3-ylamino)-5-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

HRID 2215929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215929
C(OC(N1CCC2N(C)C3C(C(F)(F)F)=CC(NC4C=CC=CN=4)=CC=3C2C1)=O)(C)(C)C.C(OC([N:40]1[CH2:56][CH2:55][C@@H:43]2[N:44]([CH3:54])[C:45]3[C:46]([C:52]#[N:53])=[CH:47][C:48](Br)=[CH:49][C:50]=3[C@@H:42]2[CH2:41]1)=O)(C)(C)C.[Cl:57][C:58]1[C:63]([NH2:64])=[C:62]([C:65]([F:68])([F:67])[F:66])[CH:61]=[C:60]([Cl:69])[N:59]=1.CC([O-])(C)C.[Na+]>>[Cl:57][C:58]1[C:63]([NH:64][C:48]2[CH:49]=[C:50]3[C:45](=[C:46]([C:52]#[N:53])[CH:47]=2)[N:44]([CH3:54])[C@H:43]2[CH2:55][CH2:56][NH:40][CH2:41][C@@H:42]32)=[C:62]([C:65]([F:66])([F:67])[F:68])[CH:61]=[C:60]([Cl:69])[N:59]=1

Komponenten

5

Edukt 4

HCID 27358982,6-Dichloro-4-(trifluoromethyl)pyridin-3-amineHCID 23676156Sodium t-butoxideHCID 58700289(4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl esterHCID 67183531HCID 67183531, Verbindung

Produkt 1

HCID 58700357(4aS,9bR)-8-(2,6-dichloro-4-trifluoromethyl-pyridin-3-ylamino)-5-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

Versuchsvorschrift

The title compound was prepared by following the general method for (5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-pyridin-3-yl-amine (Method A) as an oil (35 mg, 16%) from (4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (Example 158, 196 mg, 0.5 mmol), 2,6-dichloro-4-trifluoromethyl-pyridin-3-ylamine(186 mg, 1.5 mmol) and NaOt-Bu (144 mg, 1.5 mmol). MS (ESI): 443 (base, M+H).

Quellen und Nachweise

ORD-Eintrag
ord-6439afa2066348f8a65db3fb50cca163
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109339B2

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