4-(4-Methylbenzyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazol-3-one → HCID 9802113, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:18])[NH:11][NH:12][C:13]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]2[C:28]([O:36][C@@H:37]3[O:54][C@H:53]([CH2:55][O:56][C:57](=[O:59])[CH3:58])[C@@H:48]([O:49][C:50](=[O:52])[CH3:51])[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@H:38]3[O:39][C:40](=[O:42])[CH3:41])=[N:29][NH:30][C:31]=2[C:32]([F:35])([F:34])[F:33])=[CH:22][CH:21]=1>>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]2[C:28]([O:36][C@@H:37]3[O:54][C@H:53]([CH2:55][O:56][C:57](=[O:59])[CH3:58])[C@@H:48]([O:49][C:50](=[O:52])[CH3:51])[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@H:38]3[O:39][C:40](=[O:42])[CH3:41])=[N:29][NH:30][C:31]=2[C:32]([F:35])([F:34])[F:33])=[CH:22][CH:21]=1.[C@@H:37]1([O:18][C:10]2[C:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[C:13]([C:14]([F:17])([F:16])[F:15])[NH:12][N:11]=2)[O:54][C@H:53]([CH2:55][OH:56])[C@@H:48]([OH:49])[C@H:43]([OH:44])[C@H:38]1[OH:39]Participants
4
Procedure
4-[(4-Methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 1,2-dihydro-4-[(4-methylphenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one. Then, the title compound was prepared in a similar manner to that described in Reference Example 37 using 4-[(4-methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole instead of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole.
Sources & evidence
- ORD record
- ord-4a61894cda3b4c6abd48e6bd91a4d8c3
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429568B2
Reaction notes
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