2-Aminothiazole → 4-[(3R,3'S)-3-(3,5-Dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]-N-(thiazol-2-yl)benzenesulfonamide

HRID 1098678Notes

Reaction equation

HRID 1098678 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:9]=[C:10]([C@H:15]2[CH2:19][CH2:18][N:17]([C@H:20]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=4)[C:21]3=[O:35])[CH2:16]2)[CH:11]=[C:12]([Cl:14])[CH:13]=1>N1C=CC=CC=1.CS(C)=O>[Cl:14][C:12]1[CH:11]=[C:10]([C@H:15]2[CH2:19][CH2:18][N:17]([C@H:20]3[CH2:24][CH2:23][N:22]([C:25]4[CH:26]=[CH:27][C:28]([S:31]([NH:1][C:2]5[S:3][CH:4]=[CH:5][N:6]=5)(=[O:32])=[O:33])=[CH:29][CH:30]=4)[C:21]3=[O:35])[CH2:16]2)[CH:9]=[C:8]([Cl:7])[CH:13]=1

Participants

5

Reactant 2

HCID 21552-AminothiazoleHCID 866377574-[(3R,3'S)-3-(3,5-dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]benzene-1-sulfonyl chloride

Product 1

HCID 446034274-[(3R,3'S)-3-(3,5-Dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]-N-(thiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

Synthesized according to General Procedure 12, Method A: To a solution of 2-aminothiazole (15.9 mg, 0.16 mmol) in pyridine (0.4 mL) was added 4-[(3R,3′S)-3-(3,5-dichlorophenyl)-2′-oxo-1,3′-bipyrrolidin-1′-yl]benzene-1-sulfonyl chloride (25 mg, 0.05 mmol) and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was diluted with DMSO, filtered and purified by reverse phase HPLC using 5%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to afford the desired product.

Workup

  1. customSynthesized
  2. filtrationfiltered
  3. custompurified by reverse phase

Sources & evidence

ORD record
ord-7b4123198f30479ebb3f0b1127127ba3
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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