5-(5-chloro-1,2,4-thiadiazol-3-yl)thiophene-2-sulfonyl Chloride → 5-(5-Chloro-1,2,4-thiadiazol-3-yl)-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide

HRID 130466Notes

Reaction equation

HRID 130466 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[Cl:18][C:19]1[S:23][N:22]=[C:21]([C:24]2[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=2)[N:20]=1>ClCCl.N1C=CC=CC=1>[Cl:18][C:19]1[S:23][N:22]=[C:21]([C:24]2[S:28][C:27]([S:29]([NH:14][C:13]3[CH:15]=[C:9]([N:4]4[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]4)[CH:10]=[CH:11][C:12]=3[O:16][CH3:17])(=[O:31])=[O:30])=[CH:26][CH:25]=2)[N:20]=1

Participants

5

Reactant 2

HCID 27358205-(5-chloro-1,2,4-thiadiazol-3-yl)thiophene-2-sulfonyl ChlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 116847515-(5-Chloro-1,2,4-thiadiazol-3-yl)-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (33 mg, 0.14 mmol) in dichloromethane (2 ml) and pyridine (0.5 ml) was treated with 5-(5-chloro-1,2,4-thiadiazol-3-yl)-2-thiophenesulfonyl chloride (50 mg, 0.17 mmol) and the resulting mixture stirred at room temperature overnight. The mixture was then concentrated in vacuo, co-evaporated with toluene and the crude product purified by mass directed autoprep HPLC to afford the desired product which was characterized as the hydrochloride salt. MS (ES+) m/e 500/502 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo, co-evaporated with toluene
  2. customthe crude product purified by mass

Sources & evidence

ORD record
ord-f2673600998b4da0b7abb280b675e6f3
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

Loading…