1-Methylimidazole → HCID 118661240, compound

HRID 64046Notes

Reaction equation

HRID 64046 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C@@H:5]1[CH2:10][C@@H:9]([NH:11][S:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:14])=[O:13])[C@H:8]([OH:23])[CH2:7][CH2:6]1)=[O:4].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.CN1C=CN=C1>ClCCl>[CH3:35][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:23][C@@H:8]2[CH2:7][CH2:6][C@H:5]([C:3](=[O:4])[N:2]([CH3:1])[CH3:24])[CH2:10][C@H:9]2[NH:11][S:12](=[O:13])(=[O:14])[NH:15][C:16]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:22])(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 118671017Edoxaban Impurity 158

Product 1

HCID 118661240HCID 118661240, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl {[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]sulfamoyl}carbamate (200 mg) was dissolved in dichloromethane (2.0 mL), and p-toluenesulfonyl chloride (136 mg) and N-methylimidazole (87.0 mL) were then added to the obtained solution. The obtained mixture was stirred at room temperature for approximately 20 hours. Thereafter, the reaction mixture was purified by silica gel column chromatography to obtain the title compound (107 mg, yield: 38%) in the form of powder.

Workup

  1. customThereafter, the reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b4e7473e492f48f7becd710944484f7d
Source dataset
uspto-grants-2016_09
Patent number
US09447118B2

Reaction notes

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