5-bromo-3,6-diethyl-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine

HRID 1612229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612229
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.Br[C:31]1[N:32]=[C:33]([CH2:52][CH3:53])[C:34]([NH:39][CH:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[O:50][CH3:51])[CH2:43][CH2:42][CH2:41]2)=[N:35][C:36]=1[CH2:37][CH3:38]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:31]1[N:32]=[C:33]([CH2:52][CH3:53])[C:34]([NH:39][CH:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[O:50][CH3:51])[CH2:43][CH2:42][CH2:41]2)=[N:35][C:36]=1[CH2:37][CH3:38]

Komponenten

5

Edukt 2

HCID 221475095-bromo-3,6-diethyl-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amineHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Produkt 1

HCID 221473155-(2,4-dichlorophenyl)-3,6-diethyl-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting 5-bromo-3,6-diethyl-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine, ethylene glycol dimethyl ether and tetrakis(triphenylphosphine) palladium and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.50, 7.34-7.22, 6.83, 5.46, 4.45, 3.75, 2.94-2.79, 2.60-2.53, 1.92-1.77, 1.28-1.16; HRMS (FAB) calcd for C25H27Cl2N3O+H 456.1609, found 456.1602.

Quellen und Nachweise

ORD-Eintrag
ord-ebc3206102594150a7f736bb961ee06a
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992087B2

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