5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine → cis-(+/-)-N-[4-ethoxytetrahydrofuran-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine
Reaction equation
Cl[C:2]1C=C(Cl)C=C[C:3]=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[CH2:32]([C:34]1[C:35]([NH:51][C@H:52]2[CH2:56][O:55][CH2:54][C@H:53]2[OH:57])=[N:36][C:37]([CH2:49][CH3:50])=[C:38]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:41]=2[CH3:48])[N:39]=1)[CH3:33]>>[CH2:2]([O:57][C@H:53]1[CH2:54][O:55][CH2:56][C@H:52]1[NH:51][C:35]1[C:34]([CH2:32][CH3:33])=[N:39][C:38]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][C:41]=2[CH3:48])=[C:37]([CH2:49][CH3:50])[N:36]=1)[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
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 of cis-(+/−)-4-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol and making non-critical variations provided the title compound as a light yellow solid. IR (liq.) 2972, 2935, 2874, 1609, 1564, 1481, 1395, 1294, 1243, 1204, 1160, 1123, 1077, 1069, 1058 cm−1; OAMS supporting ions at: ESI+ 386.2; MS (EI) m/z 385 (M+); HRMS (FAB) calcd for C22H31N3O3+H1 386.2443, found 386.2457. Anal. Calcd for C22H31N3O3: C, 68.54; H, 8.11; N, 10.90. Found: C, 68.22; H, 8.05; N, 10.76.
Sources & evidence
- ORD record
- ord-1055392fb4d14d3bb25cf7c0ba28c6f1
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06992087B2
Reaction notes
Loading…