2-Amino-2-methylpropanamide → 3-(beta-D-Galactopyranosyloxy)-5-isopropyl-4-{[4-(2-{1-[(4-methylpiperazin-1-yl)carbonyl]-1-(methyl)-ethylcarbamoyl}ethoxy)phenyl]methyl}-1H-pyrazole

HRID 2223644Notes

Reaction equation

HRID 2223644 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][C:40](O)=[O:41])=[CH:33][CH:32]=2)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[NH2:46][C:47]([CH3:58])([CH3:57])[C:48]([N:50]1[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]1)=[O:49].NC(C)(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][C:40](=[O:41])[NH:46][C:47]([C:48]([N:50]4[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]4)=[O:49])([CH3:58])[CH3:57])=[CH:33][CH:32]=3)=[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

HCID 64537832-Amino-2-methylpropanamideHCID 230778602-Amino-2-methyl-1-(4-methylpiperazin-1-yl)propan-1-oneHCID 685404693-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyloxy)-4-{[4-(2-carboxyethoxy)phenyl]-methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 685387623-(beta-D-Galactopyranosyloxy)-5-isopropyl-4-{[4-(2-{1-[(4-methylpiperazin-1-yl)carbonyl]-1-(methyl)-ethylcarbamoyl}ethoxy)phenyl]methyl}-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 78 using 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-{[4-(2-carboxyethoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 1-(2-amino-2-methylpropionyl)-4-methylpiperazine instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(2-carboxyethoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methylpropionamide, respectively.

Sources & evidence

ORD record
ord-a29f58278ba3492da242cf1fd9c5e92d
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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