HCID 67341040, compound → HCID 67341429, compound

HRID 1673290Notes

Reaction equation

HRID 1673290 reaction equation
[C:1]([O:7][C@@H:8]1[C@@H:13]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:12]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C@@H:11]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:10][C@H:9]1[O:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][C:44]=2/[CH:46]=[CH:47]/[C:48]2[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=2)[NH:39][N:38]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>O1CCCC1.[C].[Pd]>[C:1]([O:7][C@@H:8]1[C@@H:13]([O:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:18])[CH3:19])[C@H:12]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C@@H:11]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:32])[CH3:33])[O:10][C@H:9]1[O:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][C:44]=2[CH2:46][CH2:47][C:48]2[CH:49]=[CH:50][N:51]=[CH:52][CH:53]=2)[NH:39][N:38]=1)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

4

Reactant 1

HCID 67341040HCID 67341040, compound

Product 1

HCID 67341429HCID 67341429, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-4-[(E)-2-(pyridin-4-yl)vinyl]-1H-indazole (0.13 g) in tetrahydrofuran (6 mL) was added 10% palladium-carbon powder (26 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give 3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-4-[2-(pyridin-4-yl)ethyl]-1H-indazole (0.13 g). This material was dissolved in methanol (6 mL). To the solution was added sodium methoxide (28% methanol solution, 0.12 mL), and the mixture was stirred at 50° C. overnight. To the reaction mixture was added acetic acid (0.05 mL), and the resulting mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1 containing triethylamine at 3%) to give the title compound (70 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f012b0d849642dbb9a68c49f1a74e5a
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

Loading…