1-Iodopropane → cis-(+/-)-5-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[4-propoxytetrahydrofuran-3-yl]pyrazin-2-amine

HRID 1612312Notes

Reaction equation

HRID 1612312 reaction equation
Cl[C:2]1[CH:7]=C(Cl)C=C[C:3]=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]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:41]1[N:42]=[C:43]([CH2:56][CH3:57])[C:44]([NH:49][C@H:50]2[CH2:54][O:53][CH2:52][C@H:51]2[OH:55])=[N:45][C:46]=1[CH2:47][CH3:48].ICCC>>[Cl:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:41]1[N:42]=[C:43]([CH2:56][CH3:57])[C:44]([NH:49][C@H:50]2[C@@H:51]([O:55][CH2:3][CH2:2][CH3:7])[CH2:52][O:53][CH2:54]2)=[N:45][C:46]=1[CH2:47][CH3:48]

Participants

4

Reactant 3

HCID 336431-IodopropaneHCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 86588878cis-(+/-)-4-{[5-(2-Chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}tetrahydrofuran-3-ol

Product 1

HCID 10127037cis-(+/-)-5-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[4-propoxytetrahydrofuran-3-yl]pyrazin-2-amine

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-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}tetrahydrofuran-3-ol and 1-iodopropane and making non-critical variations provided the title compound as a light yellow oil. IR (liq.) 2967, 2936, 2875, 1606, 1566, 1483, 1441, 1396, 1287, 1230, 1203, 1124, 1078, 1058, 1046 cm−1; OAMS supporting ions at: ESI+ 420.2; MS (EI) m/z 419 (M+); HRMS (FAB) calcd for C22H30CLN3O3+H1 420.2054, found 420.2052. Anal. Calcd for C22H30ClN3O3: C, 62.92; H, 7.20; N, 10.01. Found: C, 62.78; H, 7.28; N, 10.01.

Sources & evidence

ORD record
ord-92ca9006524f4dfe970dacc1ed49d2d4
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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