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

HRID 1265022Notes

Reaction equation

HRID 1265022 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[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[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[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[CH3:30])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53756172N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[2-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 12044908N-(4-chloro-3-methyl-5-isoxazolyl)-2-[2-methyl-4, 5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamideYield 63.7%

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-methyl-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide (0.13 g, 0.23 mmoles), methanol (6 ml) and 4N HCl (2 ml). Recrystallization from chloroform/hexanes provided 70 mg (63%) of the title compound as a white crystalline solid, m.p. 182-184° C.

Workup

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

Sources & evidence

ORD record
ord-f82c4fd535c047fdbeaed97775ffc9a4
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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