Sodium Iodide → HCID 67340941, compound

HRID 1673324Notes

Reaction equation

HRID 1673324 reaction equation
[C@@H:1]1([O:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([CH2:40][OH:41])([CH2:38][OH:39])[CH2:36][OH:37])=[CH:26][CH:25]=3)[NH:15][N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].Br[CH2:43][C:44]([NH2:46])=[O:45].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C)C=O.O>[C:44]([CH2:43][N:15]1[C:16]2[C:21](=[C:20]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([CH2:36][OH:37])([CH2:40][OH:41])[CH2:38][OH:39])=[CH:26][CH:25]=3)[CH:19]=[CH:18][CH:17]=2)[C:13]([O:12][C@@H:1]2[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]2[OH:3])=[N:14]1)(=[O:45])[NH2:46]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 11519846HCID 11519846, compound

Product 1

HCID 67340941HCID 67340941, compoundYield 11.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(β-D-glucopyranosyloxy)-4-[2-(4-{3-[2-hydroxy-1,1-bis(hydroxymethyl)ethylamino]propoxy}phenyl)-ethyl]-1H-indazole (57 mg), 2-bromoacetoamide (41 mg), cesium carbonate (97 mg) and a catalytic amount of sodium iodide in N,N-dimethylformamide (1 mL) was stirred at room temperature overnight. To the reaction mixture was added water, and the resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) and preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/methanol=90/10-10/90) successively to give the title compound (7 mg).

Workup

  1. distillationthe resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) and preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/methanol=90/10-10/90) successively

Sources & evidence

ORD record
ord-89149f2de00b443bb6d32b38aca00118
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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