(1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol → (1R,2R)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoate
Reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([C:8]([O:10][C@H:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@@H:12]2[NH:20][C:21]2[C:26]([CH2:27][CH3:28])=[N:25][C:24]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])=[C:23]([CH2:37][CH3:38])[N:22]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(C1C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC(CC)=CN=1)C>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C@@H:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]2[NH:20][C:21]2[C:26]([CH2:27][CH3:28])=[N:25][C:24]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])=[C:23]([CH2:37][CH3:38])[N:22]=2)=[O:9])=[CH:39][CH:40]=1)([O-:3])=[O:2]Participants
3
Reactant 2
Product 1
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 (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol and making non-critical variations provided the title compound as a yellow solid. IR (diffuse reflectance) 1725, 1568, 1550, 1527, 1498, 1467, 1392, 1372, 1349, 1320, 1273, 1119, 1103, 1014, 719 cm−1; OAMS supporting ions at: ESI+ 577.1; MS (CI) m/z 577 (MH+); HRMS (FAB) calcd for C30H26CL2N4O4+H1 577.1409, found 577.1393; [α]25D=−118 (c 0.62, methylene chloride).
Sources & evidence
- ORD record
- ord-25111fca44b24afc9f87f6d74c7a98f8
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041672B2
Reaction notes
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