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 2261488Notes

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

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

customSynthesized
stirringthe reaction mixture was stirred at RT for 16 hours
filtrationfiltered
custompurified by reverse phase

Sources & evidence

ORD record: ord-8f82fedfc0574701b36d47f12215469c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846954B2

Reaction notes

Loading…