2,4-Dimethylbenzaldehyde → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2,4-dimethylbenzyl]thieno[2,3-b]pyridine-3-sulfonamide

HRID 2268996Notes

Reaction equation

HRID 2268996 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[N:4][O:5][C:6]=1[N:7]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][CH:12]=1)(=[O:10])=[O:9].[Li]C(C)(C)C.[CH3:32][C:33]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:34]=1[CH:35]=[O:36]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:26])=[N:4][O:5][C:6]=1[N:7]([CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[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:35]([OH:36])[C:34]1[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:33]=1[CH3:32])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 618142,4-DimethylbenzaldehydeHCID 18614049N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamideHCID 178418306HCID 178418306, compound

Product 1

HCID 54206612N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2,4-dimethylbenzyl]thieno[2,3-b]pyridine-3-sulfonamideYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the method of Example 4(B) using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamide (0.18 g, 0.42 mmoles)[Example 4(A)], t-BuLi (1.7 M, 0.32 ml, 0.55 mmoles), THF (5 ml) and 2,4-dimethylbenzaldehyde (0.12 ml, 0.84 mmoles). Flash chromatography (40% EtOAc/hexanes) provided 0.17 g (73%) of the title compound.

Workup

  1. customThe title compound was prepared by the method of Example 4(B)

Sources & evidence

ORD record
ord-48c7b8a29f0f495aaee7febb54e70553
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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