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

HRID 2215921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215921
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.[F:57][C:58]([F:67])([F:66])[C:59]1[CH:64]=[CH:63][N:62]=[CH:61][C:60]=1[NH2:65].CC([O-])(C)C.[Na+]>>[CH3:54][N:44]1[C:45]2[C:50](=[CH:49][C:48]([NH:65][C:60]3[CH:61]=[N:62][CH:63]=[CH:64][C:59]=3[C:58]([F:67])([F:57])[F:66])=[CH:47][C:46]=2[C:52]#[N:53])[C@@H:42]2[CH2:41][NH:40][CH2:56][CH2:55][C@H:43]12

Komponenten

5

Edukt 4

HCID 27359573-Amino-4-(trifluoromethyl)pyridineHCID 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 58700425(4aS,9bR)-5-methyl-8-(4-trifluoromethyl-pyridin-3-ylamino)-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 a yellow solid (50 mg, 26%) 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), 4-trifluoromethyl-pyridin-3-ylamine (141 mg, 1.5 mmol) and NaOt-Bu (144 mg, 1.5 mmol). MS (ESI): 374 (base, M+H).

Quellen und Nachweise

ORD-Eintrag
ord-d5abb7455b64411aa51ceff984d8922b
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109339B2

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