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

HRID 1612304Notes

Reaction equation

HRID 1612304 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([C:8](O[C@H]2CC3C(=CC=CC=3)[C@@H]2NC2C(CC)=NC(C3C=CC(Cl)=CC=3Cl)=C(CC)N=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:41]([C:43]1[C:44]([NH:60][C@@H:61]2[CH2:65][O:64][CH2:63][C@H:62]2[OH:66])=[N:45][C:46]([CH2:58][CH3:59])=[C:47]([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][C:50]=2[CH3:57])[N:48]=1)[CH3:42]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:66][C@H:62]2[C@@H:61]([NH:60][C:44]3[C:43]([CH2:41][CH3:42])=[N:48][C:47]([C:49]4[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][C:50]=4[CH3:57])=[C:46]([CH2:58][CH3:59])[N:45]=3)[CH2:65][O:64][CH2:63]2)=[O:9])=[CH:39][CH:40]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 58583503(1S,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoateHCID 86588873trans-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

Product 1

HCID 58583491cis-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-yl 4-nitrobenzoate

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-yl 4-nitrobenzoate but substituting trans-(+/−)-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 semi-solid. MS (ESI+) for m/z 507.1 (M+H)+.

Sources & evidence

ORD record
ord-5e6d7a36e1534ddc8e52222dfdfc75d5
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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