HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,4-Dimethylbenzaldehyde | HCID 61814 | — |
| Reactant | N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)thieno[2,3-b]pyridine-3-sulfonamide | HCID 18614049 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2,4-dimethylbenzyl]thieno[2,3-b]pyridine-3-sulfonamide | HCID 54206612 | 73.3% |
Reaction Steps
The title compound was prepared by the method of Example 4(B) using N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06013655 |
| Source dataset | uspto-grants-2000_01 |
| ORD ID | ord-715ddb3795ce44f697d9301a8efc6f20 |
| Source note | uspto-grants-2000_01 |