2-Fluoroethyl bromide → 5-[2-chloro-4-(dimethylamino)phenyl]-3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

HRID 1824050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1824050
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[Cl:32][C:33]1[CH:38]=[C:37]([N:39]([CH3:41])[CH3:40])[CH:36]=[CH:35][C:34]=1[C:42]1[N:43]=[C:44]([CH2:61][CH3:62])[C:45]([NH:50][C@@H:51]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:53][C@@H:52]2[OH:60])=[N:46][C:47]=1[CH2:48][CH3:49].Br[CH2:64][CH2:65][F:66]>>[Cl:32][C:33]1[CH:38]=[C:37]([N:39]([CH3:41])[CH3:40])[CH:36]=[CH:35][C:34]=1[C:42]1[N:43]=[C:44]([CH2:61][CH3:62])[C:45]([NH:50][C@@H:51]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:53][C@@H:52]2[O:60][CH2:64][CH2:65][F:66])=[N:46][C:47]=1[CH2:48][CH3:49]

Komponenten

4

Edukt 3

HCID 129822-Fluoroethyl bromideHCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58583286(1R,2S)-1-({5-[2-chloro-4-(dimethylamino)phenyl]-3,6-diethylpyrazin-2-yl}amino)-2,3-dihydro-1H-inden-2-ol

Produkt 1

HCID 103110485-[2-chloro-4-(dimethylamino)phenyl]-3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

Versuchsvorschrift

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting (1R,2S)-1-({5-[2-chloro-4-(dimethylamino)phenyl]-3,6-diethylpyrazin-2-yl}amino)-2,3-dihydro-1H-inden-2-ol and 1-bromo-2-fluoroethane and making non-critical variations provided the title compound as a light yellow amorphous solid. IR (diffuse reflectance) 2969, 2932, 2907, 2877, 1608, 1563, 1545, 1483, 1447, 1392, 1353, 1207, 1177, 1123, 1042 cm−1; OAMS supporting ions at: ESI+ 483.2; MS (EI) m/z 482 (M+); HRMS (FAB) calcd for C27H32CLFN4O+H1 483.2327, found 483.2324. [α]25D=−79 (c 0.52, methylene chloride); Anal. Calcd for C27H32ClFN4O: C, 67.14; H, 6.68; N, 11.60. Found: C, 67.19; H, 6.90; N, 11.63.

Quellen und Nachweise

ORD-Eintrag
ord-67ec3673d1cb4d3c928da1870ca7d752
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041672B2

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