Potassium Iodide → HCID 86758624, compound

HRID 2296675Notes

Reaction equation

HRID 2296675 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)(=[O:16])=[O:15])[C@@H:10]([C:29]([NH:31][O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)=[O:30])[CH2:9]1)(=[O:7])=[O:6].[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.[I-].[K+]>CN(C=O)C>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[S:18][C:17]([S:14]([N:11]3[CH2:12][CH2:13][N:8]([S:5]([CH2:4][CH2:3][CH2:2][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)(=[O:7])=[O:6])[CH2:9][C@@H:10]3[C:29]([NH:31][O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)=[O:30])(=[O:16])=[O:15])=[CH:21][CH:20]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 53732088HCID 53732088, compound

Product 1

HCID 86758624HCID 86758624, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-4-(3-chloropropanesulfonyl)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (200 mg), piperidine (279 mg) and potassium iodide (65 mg) in DMF (3 ml) was stirred at ambient temperature for 2 days. The mixture was concentrated in vacuo. The residue was partitioned between AcOEt and H2O. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated in vacuo. The residue was purified by SiO2 column chromatography eluted with MeOH in CHCl3 gradually from 0% to 5%, to give 165 mg of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-4-[3-(-piperidino) propanesulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was partitioned between AcOEt and H2O
  3. washThe organic layer was washed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 column chromatography
  7. washeluted with MeOH in CHCl3 gradually from 0% to 5%

Sources & evidence

ORD record
ord-d1e152bfb2574d3fba3bee412c7eba93
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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