2-Morpholinoethylamine → 4-{[4-(2-{3-[1-Carbamoyl-1-(methyl)ethyl]ureido}ethoxy)-2-methylphenyl]methyl}-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 2189361Notes

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][NH2:40])=[CH:33][C:32]=2[CH3:41])=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=O)C.[NH2:45][C:46]([CH3:51])([CH3:50])[C:47]([NH2:49])=[O:48].NCCN1CC[O:58][CH2:57]C1>>[C:47]([C:46]([NH:45][C:57](=[O:58])[NH:40][CH2:39][CH2:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:42]([CH3:44])[CH3:43])=[C:32]([CH3:41])[CH:33]=1)([CH3:51])[CH3:50])(=[O:48])[NH2:49]

Participants

Reactant 3

HCID 4082852-Morpholinoethylamine

HCID 64537832-Amino-2-methylpropanamide

HCID 689452653-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(2-aminoethoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689431704-{[4-(2-{3-[1-Carbamoyl-1-(methyl)ethyl]ureido}ethoxy)-2-methylphenyl]methyl}-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 19 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(2-aminoethoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methylpropionamide instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 4-(2-aminoethyl)morpholine, respectively.

Sources & evidence

ORD record: ord-0481177892e145ebbe3f0f80a75abb53
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324176B2

Reaction notes

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