4-Benzyl-1-[3-(2-nitrobenzenesulfonylamino)propionyl]piperazine → 3-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-{[4-(3-(2-[(4-benzylpiperazin-1-yl)carbonyl]ethylamino}propoxy)-2-methylphenyl]methyl}-1H-pyrazole

HRID 1869013Notes

Reaction equation

HRID 1869013 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][CH2:16][NH:17]S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(NCCCC[C@H](N[CH2:51][CH2:52][CH2:53][O:54][C:55]1[CH:60]=[CH:59][C:58]([CH2:61][C:62]2[C:63]([O:70][C@@H:71]3[O:79][C@H:78]([CH2:80][OH:81])[C@@H:76]([OH:77])[C@H:74]([OH:75])[C@H:72]3[OH:73])=[N:64][NH:65][C:66]=2[CH:67]([CH3:69])[CH3:68])=[C:57]([CH3:82])[CH:56]=1)C(=O)N)=O)C1C=CC=CC=1>>[C@@H:71]1([O:70][C:63]2[C:62]([CH2:61][C:58]3[CH:59]=[CH:60][C:55]([O:54][CH2:53][CH2:52][CH2:51][NH:17][CH2:16][CH2:15][C:14]([N:11]4[CH2:10][CH2:9][N:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:13][CH2:12]4)=[O:30])=[CH:56][C:57]=3[CH3:82])=[C:66]([CH:67]([CH3:68])[CH3:69])[NH:65][N:64]=2)[O:79][C@H:78]([CH2:80][OH:81])[C@@H:76]([OH:77])[C@H:74]([OH:75])[C@H:72]1[OH:73].[C@@H:71]1([O:70][C:63]2[C:62]([CH2:61][C:58]3[CH:59]=[CH:60][C:55]([O:54][CH2:53][CH2:52][CH2:51][NH:17][CH2:16][CH2:15][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[O:30])=[CH:56][C:57]=3[CH3:82])=[C:66]([CH:67]([CH3:68])[CH3:69])[NH:65][N:64]=2)[O:79][C@H:78]([CH2:80][OH:81])[C@@H:76]([OH:77])[C@H:74]([OH:75])[C@H:72]1[OH:73]

Participants

4

Reactant 2

HCID 230788784-Benzyl-1-[3-(2-nitrobenzenesulfonylamino)propionyl]piperazineHCID 689410364-[(4-{3-[(S)-5-Benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Product 2

HCID 689441003-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-{[4-(3-(2-[(4-benzylpiperazin-1-yl)carbonyl]ethylamino}propoxy)-2-methylphenyl]methyl}-1H-pyrazoleHCID 689459523-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-{[4-(3-{2-[(piperazin-1-yl)carbonyl]ethylamino}propoxy)-2-methylphenyl]methyl}-1H-pyrazole

Procedure

3-(β-D-Glucopyranosyloxy)-5-isopropyl-4-{[4-(3-{2-[(4-benzylpiperazin-1-yl)carbonyl]ethylamino}propoxy)-2-methylphenyl]methyl}-1H-pyrazole was prepared in a similar manner to that described in Example 51 using 4-benzyl-1-[3-(2-nitrobenzenesulfonylamino)propionyl]piperazine instead of 2-methyl-2-(2-nitrobenzenesulfonylamino)propionamide. Then the title compound was prepared in a similar manner to that described in Example 79 using this material instead of 4-[(4-{3-[(S)-5-benzyloxycarbonylamino-1-(carbamoyl)pentylamino]propoxy}-2-methylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole.

Sources & evidence

ORD record
ord-5c0fd9bd0c394922943d27ca67cc44af
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

Loading…