Potassium Carbonate → HCID 178490673, compound

HRID 2196796Notes

Reaction equation

HRID 2196796 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O[CH2:33][C@@H:34]2[CH2:38][CH2:37][C:36](=[O:39])[NH:35]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:33][C@@H:34]2[CH2:38][CH2:37][C:36](=[O:39])[NH:35]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734055[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonateHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Product 1

HCID 178490673HCID 178490673, compoundYield 48.5%

Reagents, catalysts & solvents 4

HCID 6225Tetraethylammonium IodideCatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 4C (810 mg, 2.49 mmol), (S)-(5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate (Aldrich, 807 mg, 3 mmol), potassium carbonate (828 mg, 6 mmol), tetrabutylammonium iodide (20 mg, 0.05 mmol), tetrabutylammonium hydrogensulfate (20 mg, 0.06 mmol) and tetraethylammonium iodide (20 mg, 0.07 mmol) in anhydrous toluene (100 mL) was refluxed for 15 h. The mixture was cooled to room temperature, washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed (SiO2, ethyl acetate-ethanol 9:1) to afford 510 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.32 (s, 9H), 1.83 (m, 1H), 2.07 (m, 3H), 3.78 (s, 3H), 4.09 (m, 2H), 4.30 (m, 1H), 7.10 (d, J=9 Hz, 1H), 7.27 (s, 1H), 7.45 (dd, J=9 Hz, 3 Hz, 1H), 7.62 (d, J=3 Hz, 1H), 7.82 (broad s, 1H); MS (DCI/NH3) m/z 422 (M+H)+. Anal. calcd for C20H24ClN3O3S.0.25H2O: C, 56.33; H, 5.79; N, 9.85. Found: C, 56.42; H, 5.55; N, 9.25.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed (SiO2, ethyl acetate-ethanol 9:1)

Sources & evidence

ORD record
ord-403f679a22464383b4441d3f041412a8
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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