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

HRID 2269006Notes

Reaction equation

HRID 2269006 reaction equation
[Cl:1][C:2]1[C:3]([CH3:42])=[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[CH2:30][CH2:31][O:32]C(=O)C)(=[O:10])=[O:9].Cl>CO>[Cl:1][C:2]1[C:3]([CH3:42])=[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[CH2:30][CH2:31][OH:32])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18614040N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-{2-[2-(acetoxy)ethyl]-4,5-(methylenedioxy)benzyl}thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 12044910N-(4-chloro-3-methyl-5-isoxazolyl)-2-[2-(2-hydroxyethyl)-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamideYield 84%

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-[2-(acetoxy)ethyl]-4,5-(methylenedioxy)benzyl}thieno[2,3-b]pyridine-3-sulfonamide (83 mg, 0.13 mmoles), methanol (3 ml) and 4N HCl (1 ml). Recrystallization from CH2Cl2/hexanes provided 55 mg (84%) of the title compound as a white solid, m.p. 104-106° C.

Workup

  1. customThe title compound was prepared by the method of Example 4(D)
  2. customRecrystallization from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-9684cb368ff441e4a5bd8a4f09a9ddf7
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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