HCID 18614055, compound → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3-(3,4-methylenedioxyphenyl)propionyl]thieno[2,3-b]pyridine-3-sulfonamide

HRID 2393158Notes

Reaction equation

HRID 2393158 reaction equation
[Cl:1][C:2]1[C:3]([CH3:39])=[N:4][O:5][C:6]=1[N:7]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20]([OH:32])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)(=[O:10])=[O:9].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:39])=[N:4][O:5][C:6]=1[N:7]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[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:32])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 18614055HCID 18614055, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18614039N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3-(3,4-methylenedioxyphenyl)propionyl]thieno[2,3-b]pyridine-3-sulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the method of Example 12(B) using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[1-hydroxy-3-(3,4-methylenedioxyphenyl)propyl]thieno[2,3-b]pyridine-3-sulfonamide (0.51 g, 0.85 mmoles), CH2Cl2 (20 ml), celite, and PCC (0.27 g, 1.3 mmoles) except the reaction mixture was stirred 24 hours prior to filtering. Flash chromatography (40% EtOAc/hexanes) provided 0.37 g (74%) of the title compound as a yellow oil/solid.

Workup

  1. customThe title compound was prepared by the method of Example 12(B)
  2. filtrationto filtering

Sources & evidence

ORD record
ord-abb75b2c7d40412b8f6eb0d07321e815
Source dataset
uspto-grants-1998_09
Patent number
US05804585

Reaction notes

Loading…