N-[3-(dimethylamino)propyl]-2-nitrobenzenesulfonamide → 3-(beta-D-Galactopyranosyloxy)-5-isopropyl-4-[(4-{3-[3-(dimethylamino)propylamino]propoxy}-2-methylphenyl)-methyl]-1H-pyrazole
Reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40]O)=[CH:33][C:32]=2[CH3:42])=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[CH3:46][N:47]([CH3:64])[CH2:48][CH2:49][CH2:50][NH:51]S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O.CC(NS(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)(C)C(N)=O>>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][NH:51][CH2:50][CH2:49][CH2:48][N:47]([CH3:64])[CH3:46])=[CH:33][C:32]=3[CH3:42])=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner to that described in Example 51 using 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and N,N-dimethyl-N′-(2-nitrobenzenesulfonyl)-1,3-diaminopropane instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-methyl-2-(2-nitrobenzenesulfonylamino)-propionamide, respectively.
Sources & evidence
- ORD record
- ord-fb939b07c59c43228c1f8d0ae5dcf24a
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635684B2
Reaction notes
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