2-Amino-2-methyl-1-propanol → 3-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-({4-[3-(3-pyridyl-methylamino)propoxy]phenyl}methyl)-1H-pyrazole

HRID 2189378Notes

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]O)=[CH:33][CH:32]=2)=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=O)C.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47](CN)[CH:46]=1.[NH2:53][C:54](C)(C)CO>>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:53]([C:47]4[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=4)[CH3:54])=[CH:35][CH:36]=3)=[C:28]([CH:42]([CH3:43])[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 118072-Amino-2-methyl-1-propanol

HCID 310183-Pyridinemethanamine

HCID 689429023-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689445783-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-({4-[3-(3-pyridyl-methylamino)propoxy]phenyl}methyl)-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 57 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 3-picolylamine instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methyl-1-propanol, respectively.

Sources & evidence

ORD record: ord-170a5bbf460341418e507f400e782512
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324176B2

Reaction notes

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