4-Chloro-3-methyl-1,2-oxazol-5-amine → HCID 23445514, compound

HRID 1166974Notes

Reaction equation

HRID 1166974 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[NH2:17][C:18]1[O:22][N:21]=[C:20]([CH3:23])[C:19]=1[Cl:24]>>[Cl:24][C:19]1[C:20]([CH3:23])=[N:21][O:22][C:18]=1[NH:17][S:2]([C:5]1[S:6][C:7]([C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 105828224-Chloro-3-methyl-1,2-oxazol-5-amineHCID 21843505HCID 21843505, compound

Product 1

HCID 23445514HCID 23445514, compoundYield 71.1%

Procedure

N-(4-chloro-3-methyl-5-isoxazolyl)-5-(5-ethyl-2-thienyl)thiophene-2-sulfonamide was prepared in the same manner as in Example 2. Reaction of 2-chlorosulfonyl-5-(5-ethyl-2-thienyl)thiophene (Example 140C, 200 mg, 0.68 mmol) with 5-amino-4-chloro-3-methylisoxazole (91 mg, 0.68 mmol) yielded 188 mg of the final product (71% yield). A small portion of the product was further purified by preparative HPLC to give the pure sulfonamide as a tan colored solid.

Workup

  1. customN-(4-chloro-3-methyl-5-isoxazolyl)-5-(5-ethyl-2-thienyl)thiophene-2-sulfonamide was prepared in the same manner as in Example 2

Sources & evidence

ORD record
ord-f5f7d0a87d984a30aebe8730eeb083a2
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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