Ethanolamine → 3-(beta-D-Glucopyranosyloxy)-4-[(4-(3-[3-(2-hydroxyethyl)ureido]propoxy)-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole

HRID 1868979Notes

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][CH2:40][NH2:41])=[CH:33][C:32]=2[CH3:42])=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[NH2:46][CH2:47][CH2:48][OH:49].NCCN1CC[O:56][CH2:55]C1>>[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][CH2:40][NH:41][C:55]([NH:46][CH2:47][CH2:48][OH:49])=[O:56])=[CH:33][C:32]=3[CH3:42])=[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

Reactant 3

HCID 700Ethanolamine

HCID 4082852-Morpholinoethylamine

HCID 689401203-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)-2-methylphenyl]-methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689405233-(beta-D-Glucopyranosyloxy)-4-[(4-(3-[3-(2-hydroxyethyl)ureido]propoxy)-2-methylphenyl)methyl]-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-(3-aminopropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-aminoethanol 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-aedbe72e4a1f433c854a9df4f790f873
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635684B2

Reaction notes

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