Pyridine → HCID 21186216, compound

HRID 1107464Notes

Reaction equation

HRID 1107464 reaction equation
[Cl:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH3:21])=[CH:15][N:14]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[C:7]([S:8]([NH:12][C:13]2[C:18]([O:19][CH3:20])=[N:17][C:16]([CH3:21])=[CH:15][N:14]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 102199682-Chloropyridine-3-sulfonyl chlorideHCID 107018943-Methoxy-5-methyl-2-pyrazinamine

Product 1

HCID 21186216HCID 21186216, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (0.1 g) was added to a solution of 2-chloropyridine-3-sulphonyl chloride (1.06 g), 2-amino-3-methoxy-5-methylpyrazine (0.695 g) and pyridine (0.424 ml) in dichloromethane (5 ml) and the mixture was stirred at ambient temperature for 18 hours. The solution was then transferred to a silica gel Mega Bond Elut column. Elution with 0-40% ethyl acetate/hexane gave 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.47 g) as an oil; 1H NMR (c6 -DMSO): 2.3 (s, 3H), 3.9 (s, 3H), 7.5 (s, 1H), 7.65 (dd, 1H), 8.45 (dd, 1H), 8.7 (dd, 1H); mass spectrum (+ve CI): 315 (M+H)+.

Workup

  1. washElution with 0-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8158d7f52386493895fc4e7dff06fcfd
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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