(1S,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol → cis-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

HRID 1824221Notes

Reaction equation

HRID 1824221 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.[N+](C1C=CC(C([O:39][C@H:40]2[C@@H:44]([NH:45][C:46]3[C:51]([CH2:52][CH3:53])=[N:50][C:49]([C:54]4[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=4[CH3:62])=[C:48]([CH2:63][CH3:64])[N:47]=3)[CH2:43][O:42][CH2:41]2)=O)=CC=1)([O-])=O>>[CH2:52]([C:51]1[C:46]([NH:45][C@H:44]2[CH2:43][O:42][CH2:41][C@H:40]2[OH:39])=[N:47][C:48]([CH2:63][CH3:64])=[C:49]([C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=2[CH3:62])[N:50]=1)[CH3:53]

Participants

3

Reactant 2

HCID 58583293(1S,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-olHCID 58583491cis-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-yl 4-nitrobenzoate

Product 1

HCID 58583303cis-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

Procedure

Following the procedure for the preparation of (1S,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol, but substituting cis-(+/−)-4-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-yl 4-nitrobenzoate and making non-critical variations provided the title compound as a colorless semi-solid. OAMS supporting ions at: ESI+ 358.2; MS (EI) m/z 357 (M+); HRMS (FAB) calcd for C20H27N3O3+H1 358.2130, found 358.2125.

Sources & evidence

ORD record
ord-10976df33da949b9b5c22f8e1eb56054
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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