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

HRID 1098679
Notes
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Reaction equation

HRID 1098679 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]([C@H:27]2[CH2:31][CH2:30][N:29]([C@H:32]3[CH2:36][CH2:35][N:34]([C:37]4[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=4)[C:33]3=[O:47])[CH2:28]2)[CH:23]=[C:24]([Cl:26])[CH:25]=1>C(#N)C>[Cl:26][C:24]1[CH:23]=[C:22]([C@H:27]2[CH2:31][CH2:30][N:29]([C@H:32]3[CH2:36][CH2:35][N:34]([C:37]4[CH:38]=[CH:39][C:40]([S:43]([NH:1][C:2]5[S:3][CH:4]=[CH:5][N:6]=5)(=[O:44])=[O:45])=[CH:41][CH:42]=4)[C:33]3=[O:47])[CH2:28]2)[CH:21]=[C:20]([Cl:19])[CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 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)benzenesulfonamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Conditions

Temperature
0 °C

Procedure

Synthesized according to General Procedure 12, Method B: To a stirred solution of 2-aminothiazole (88.8 mg, 0.89 mmol) in acetonitrile (1 mL) at 0° C. was added 2-tert-butyl-1,1,3,3-tetramethylguanidine (152 mg, 0.89 mmol) dropwise and the reaction mixture was stirred at 0° C. for 15 min. To this was slowly added a suspension of 4-[(3R,3′S)-3-(3,5-dichlorophenyl)-2′-oxo-1,3′-bipyrrolidin-1′-yl]benzene-1-sulfonyl chloride (100 mg, 0.17 mmol) in acetonitrile (0.5 mL) and the reaction mixture was stirred at 0° C. for 15 min, the cooling bath was removed and the reaction mixture was stirred at RT for 30 min. The reaction mixture was then poured into water, the pH was adjusted to ˜7 with 1M HCl, and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (0-10% MeOH in EtOAc) afforded the desired product as a solid (27 mg, 28%). 1H-NMR (400 MHz, DMSO-d6) δ 7.84-7.77 (m, 4H), 7.43-7.37 (m, 3H), 7.24 (d, J=4.6 Hz, 1H), 6.81 (d, J=4.6 Hz, 1H), 3.83-3.72 (m, 2H), 3.58 (t, J=8.8 Hz, 1H), 3.07-2.96 (m, 3H), 2.87 (td, J=8.6, 4.3 Hz, 1H), 2.34-2.20 (m, 2H), 2.11-2.02 (m, 1H) and 1.74 (dt, J=19.9, 6.9 Hz, 1H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=537.3; tR=1.21 min.

Workup

  1. customSynthesized
  2. additionTo this was slowly added
  3. stirringthe reaction mixture was stirred at 0° C. for 15 min
  4. customthe cooling bath was removed
  5. stirringthe reaction mixture was stirred at RT for 30 min
  6. additionThe reaction mixture was then poured into water
  7. extractionextracted with EtOAc (3×)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated to dryness
  11. customPurification by silica gel chromatography (0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-79e7235256514f4c972d54cb6a9817f3
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08143297B2

Reaction notes

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