Carzenide → HCID 59353043, compound

HRID 1914710Notes

Reaction equation

HRID 1914710 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([OH:3])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C1COCC1.CN(C=O)C>[F:26][CH:27]1[CH2:32][CH2:31][N:30]([C:1]([C:4]2[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=2)=[O:3])[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 8739CarzenideHCID 682631,1'-CarbonyldiimidazoleHCID 27591594-Fluoropiperidine

Product 1

HCID 59353043HCID 59353043, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-carboxybenzenesulfonamide (2 g; 9.9 mmol; 1 eq) in THF 30 mL) at 0° C. is added 1,1′-carbonyldiimidazole (1.9 g; 11.9 mmol; 1.2 eq) in one portion and the mixture is stirred for 3 h at room temperature. 4-Fluoropiperidine (3.1 g; 29.8 mmol; 3 eq) in THF (3 mL) and DMF (10 mL) is added dropwise and the mixture is stirred at room temperature for 2 h. The solvent is removed under reduced pressure and a saturated solution of NaHCO3 is added to the colourless oil which precipitates. The solid is filtered off, washed with water and dried under vacuum to afford 2.6 g (91%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.87 (d, J=8.3, 2H), 7.58 (d, J=8.3, 2H), 7.37 (br s, 2H), 4.92 (d, J=48.2, 1H), 3.67 (br s, 2H), 3.25 (br s, 2H), 1.87 (m, HPLC (max plot) 99%; Rt 1.77 min. LC/MS: (ES+) 287.0; (ES−) 285.0

Workup

  1. stirringthe mixture is stirred at room temperature for 2 h
  2. customThe solvent is removed under reduced pressure
  3. additiona saturated solution of NaHCO3 is added to the colourless oil which
  4. customprecipitates
  5. filtrationThe solid is filtered off
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-04f5bfc7dae346febb6d7567d903c5f0
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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