2-Aminothiazole → 4-[(3'S)-3-(3,5-dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]-2,6-difluoro-N-(thiazol-2-yl)benzenesulfonamide

HRID 1098686Notes

Reaction equation

HRID 1098686 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]2[CH2:31][CH2:30][N:29]([C@H:32]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[C:41]([F:43])[C:40]([S:44](Cl)(=[O:46])=[O:45])=[C:39]([F:48])[CH:38]=4)[C:33]3=[O:49])[CH2:28]2)[CH:23]=[C:24]([Cl:26])[CH:25]=1>C(#N)C.CS(C)=O>[Cl:26][C:24]1[CH:23]=[C:22]([CH:27]2[CH2:31][CH2:30][N:29]([C@H:32]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[C:41]([F:43])[C:40]([S:44]([NH:1][C:2]5[S:3][CH:4]=[CH:5][N:6]=5)(=[O:45])=[O:46])=[C:39]([F:48])[CH:38]=4)[C:33]3=[O:49])[CH2:28]2)[CH:21]=[C:20]([Cl:19])[CH:25]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 866377584-[(3'S)-3-(3,5-Dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]-2,6-difluorobenzene-1-sulfonyl chloride

Product 1

HCID 446033014-[(3'S)-3-(3,5-dichlorophenyl)-2'-oxo-1,3'-bipyrrolidin-1'-yl]-2,6-difluoro-N-(thiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Synthesized according to General Procedure 12, Method B. To a solution of 2-aminothiazole (35 mg, 0.35 mmol) in acetonitrile (0.4 mL) at 0° C. was added 2-tert-butyl-1,1,3,3-tetramethylguanidine (61 mg, 0.35 mmol) dropwise and the reaction mixture stirred at 0° C. for 10 min. 4-[(3′S)-3-(3,5-dichlorophenyl)-2′-oxo-1,3′-bipyrrolidin-1′-yl]-2,6-difluorobenzene-1-sulfonyl chloride (60 mg, 0.12 mmol) was added and the reaction mixture was stirred at RT for 16 hours. 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 4-[(3′S)-3-(3,5-dichlorophenyl)-2′-oxo-1,3′-bipyrrolidin-1′-yl]-2,6-difluoro-N-(thiazol-2-yl)benzenesulfonamide. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=573.3; tR=1.32 min.

Workup

  1. customSynthesized
  2. stirringthe reaction mixture was stirred at RT for 16 hours
  3. filtrationfiltered
  4. custompurified by reverse phase

Sources & evidence

ORD record
ord-7aee54a6e52543d5af31bea367db44f9
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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