Pyridine → HCID 57542144, compound

HRID 1809339Notes

Reaction equation

HRID 1809339 reaction equation
[Cl:1][C:2]([Cl:19])([Cl:18])[C:3]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=2)[CH2:6]1)=[O:4].[NH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1.N1C=CC=CC=1>>[S:22]1[CH:23]=[CH:24][N:25]=[C:21]1[NH:20][S:14]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][N:5]([C:3](=[O:4])[C:2]([Cl:19])([Cl:18])[Cl:1])[CH2:13]2)(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 59432940HCID 59432940, compound

Product 1

HCID 57542144HCID 57542144, compoundYield 71.4%

Conditions

Temperature
60 °C

Procedure

2-(2,2,2-Trichloro-acetyl)-2,3-dihydro-1H-isoindole-5-sulfonyl chloride (0.25 g, 0.7 mmol), was added to a stirring solution of 2-aminothiazole (0.07 g, 0.7 mmol) and pyridine (57 μl, 0.7 mmol) and heated to 60° C. for 1 h. The reaction mixture was then partitioned between CH2Cl2 and aqueous 1N HCl solution. The organic layer was concentrated in vacuo and purified via silica gel chromatography (3% MeOH in CH2Cl2) to give the sulfonamide as a tan solid (200 mg, 0.5 mmol, 67% yield). LC/MS (10-99% CH3CN), M/Z: M+1 obs=426.0; tR=2.88 min.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and aqueous 1N HCl solution
  2. concentrationThe organic layer was concentrated in vacuo
  3. custompurified via silica gel chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-76031d09b1364923b6e14595c335a667
Source dataset
uspto-grants-2013_01
Patent number
US08362032B2

Reaction notes

Loading…