5-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one → 5-Methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 7383Notes

Reaction equation

HRID 7383 reaction equation
[CH3:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1.[CH3:21][C:22]1[NH:26][N:25]=[C:24]([O:27][C@@H:28]2[O:36][C@H:35]([CH:37]([C:39](=[O:41])[CH3:40])[OH:38])[C@@:33]([C:42](=[O:44])[CH3:43])([OH:34])[C@:31]([C:45](=[O:47])[CH3:46])([OH:32])[C@@:29]2([C:48](=[O:50])[CH3:49])[OH:30])[C:23]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)=[CH:54][CH:53]=1>>[CH3:21][C:22]1[NH:26][N:25]=[C:24]([O:27][C@@H:28]2[O:36][C@H:35]([CH:37]([C:39](=[O:41])[CH3:40])[OH:38])[C@@:33]([C:42](=[O:44])[CH3:43])([OH:34])[C@:31]([C:45](=[O:47])[CH3:46])([OH:32])[C@@:29]2([C:48](=[O:50])[CH3:49])[OH:30])[C:23]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)=[CH:54][CH:53]=1.[C@@H:28]1([O:7][C:4]2[C:3]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)=[CH:11][CH:10]=3)=[C:2]([CH3:1])[NH:6][N:5]=2)[O:36][C@H:35]([CH2:37][OH:38])[C@@H:33]([OH:34])[C@H:31]([OH:32])[C@H:29]1[OH:30]

Participants

4

Reactant 2

HCID 219896955-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-oneHCID 691344045-Methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 2

HCID 691344045-Methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-beta-D-glucopyranosyloxy)-1H-pyrazoleHCID 691344513-(beta-D-Glucopyranosyloxy)-5-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-1H-pyrazole

Procedure

5-Methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-1H-pyrazole was prepared in a similar manner to that described in Example 4 using 5-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one instead of 5-methyl-4-[(4-cyclopropylphenyl)methyl]-1,2-dihydro-3H-pyrazol-3-one. Then the title compound was prepared in a similar manner to that described in Example 21 using 5-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-1H-pyrazole instead of 5-methyl-4-[(4-cyclopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole.

Sources & evidence

ORD record
ord-26f326e36a904d5e9f2369e5f379ac90
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Reaction notes

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