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

HRID 1265016Notes

Reaction equation

HRID 1265016 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[C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:10])=[O:9]>CO.Cl>[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[C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:9])=[O:10]

Participants

4

Reactant 1

HCID 18614037N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)-2-[3,4-(methylenedioxy)benzoyl]thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 15435830N-(4-chloro-3-methyl-5-isoxazolyl)-2-[3,4-(methylenedioxy)benzoyl]thieno [2,3-b]pyridine-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)-2 -[3,4-(methylenedioxy)benzoyl]thieno[2,3-b]pyridine-3-sulfonamide (0.15 g, 0.26 mmoles) in methanol (5 ml) and 4N HCl (2 ml) was heated to reflux for 3 hours then cooled to ambient temperature and concentrated. The residue was diluted with EtOAc (50 ml) and washed with saturated NaCl (2×50 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect 0.10 g (81 %) of the title compound as a foamy yellow solid, m.p. 75-90° C.

Workup

  1. temperatureto reflux for 3 hours
  2. concentrationconcentrated
  3. additionThe residue was diluted with EtOAc (50 ml)
  4. washwashed with saturated NaCl (2×50 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto collect 0.10 g (81 %) of the title compound as a foamy yellow solid, m.p. 75-90° C.

Sources & evidence

ORD record
ord-35124ea2d6d74d7ab6f281791a71cd69
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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