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

HRID 2269008Notes

Reaction equation

HRID 2269008 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:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)(=[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:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 17894960HCID 17894960, compound

Product 1

HCID 12044911N-(4-chloro-3-methyl-5-isoxazolyl)-2-(naphthylmethyl)thieno[2,3-b]pyridine-3-sulfonamideYield 63.8%

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-(naphthylmethyl)thieno[2,3-b]pyridine-3-sulfonamide (58 mg, 0.10 mmoles), methanol (2 ml) and 4N HCl (2 ml). Recrystallization from EtOAc/hexanes provided 30 mg (61%) of the title compound as a yellow crystalline solid, m.p. 165-168° 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-37718d03b80445168757c3bbd32675b4
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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