Hydrochloric Acid → N-(4-chloro-3-methyl-5-isoxazolyl)-2-(2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamide

HRID 849525Notes

Reaction equation

HRID 849525 reaction equation
[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[N:7](COCCOC)[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[O:29][CH3:30])(=[O:10])=[O:9].Cl>CO>[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[O:29][CH3:30])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18614053N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 12044912N-(4-chloro-3-methyl-5-isoxazolyl)-2-(2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamideYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by the method of Example 4(D) using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(2,6-dimethoxybenzyl)thieno[2,3-b]pyridine-3-sulfonamide (0.11 g, 0.19 mmoles), methanol (5 ml) and 4N HCl (1 ml). Recrystallization from EtOAc/hexanes provided 35 mg (39%) of the title compound as a white precipitate, m.p. 66-71° C.

Workup

  1. customThe title compound was prepared by the method of Example 4(D)
  2. customRecrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-484318b27df84739a51ae980082f4c47
Source dataset
uspto-grants-2000_01
Patent number
US06013655

Reaction notes

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