Sodium Iodide → HCID 86614385, compound

HRID 1673296Notes

Reaction equation

HRID 1673296 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][C@@H:27]4[O:53][C@H:52]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]4[O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:18]=23)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:69][C:70]([NH2:72])=[O:71].[I-].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[N:23]([CH2:69][C:70](=[O:71])[NH2:72])[N:24]=[C:25]([O:26][C@@H:27]4[O:53][C@H:52]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:48])([CH3:49])[CH3:50])[C@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]4[O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:32])[CH3:33])[C:18]=23)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 67340433HCID 67340433, compound

Product 1

HCID 86614385HCID 86614385, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-[2-(4-benzyloxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine (73 mg) in acetone (4 mL) were added cesium carbonate (56 mg), 2-bromoacetoamide (18 mg) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=30/1-10/1) to give 4-[2-(4-benzyloxyphenyl)ethyl]-1-carbamoylmethyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine (63 mg). This material was dissolved in methanol (4 mL). To the solution was added sodium methoxide (28% methanol solution, 0.027 mL), and the mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration. The crystals were washed with methanol and dried under reduced pressure to give 4-[2-(4-benzyloxyphenyl)ethyl]-1-carbamoylmethyl-3-(β-D-glucopyranosyloxy)-1H-pyrazolo-[3,4-b]pyridine (25 mg). To this material were added methanol (1 mL), tetrahydrofuran (1 mL) and 10% palladium-carbon powder (10 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (13 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=30/1-10/1)

Sources & evidence

ORD record
ord-9dbccafbfaa14a0a9de454cba2e2e5f8
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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