Hexane → HCID 46917294, compound

HRID 888261Notes

Reaction equation

HRID 888261 reaction equation
C([O-])(O)=O.[Na+].[C:6]1([S:12]([CH2:15][CH2:16][S:17][C:18]2[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:25]1([CH2:31][C:32](Cl)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CCCCCC>O1CCOCC1>[C:6]1([S:12]([CH2:15][CH2:16][S:17][C:18]2[C:23]([NH:24][C:32](=[O:33])[CH2:31][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:22][CH:21]=[CH:20][N:19]=2)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 2757989Cyclohexylacetyl chlorideHCID 67134241HCID 67134241, compound

Product 1

HCID 46917294HCID 46917294, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

336 mg (4.0 mmol) NaHCO3 were added to a solution of 294 mg (1.0 mmol) [2-[2-(benzenesulfonyl)-ethylsulfanyl]-pyridin-3-yl]amine (VPF-002) in dioxane (10 ml) and the mixture was stirred for 10 min at RT. Then 321 mg (2.0 mmol) 2-cyclohexylacetylchloride were added at 5° C. and the mixture was stirred for a further 16 h at RT. Then it was diluted with EE and filtered through kieselguhr. The filtrate was washed with a saturated aqueous NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 6:1) of the residue yielded 368 mg (0.9 mmol, 88%) N-[2-[2-(benzenesulfonyl)-ethyl-sulfanyl]-pyridin-3-yl]-2-cyclohexyl acetamide. MS: m/z 419.1 [M+H]+.

Workup

  1. stirringthe mixture was stirred for a further 16 h at RT
  2. additionThen it was diluted with EE
  3. filtrationfiltered through kieselguhr
  4. washThe filtrate was washed with a saturated aqueous NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-d3d020707b6c4e26b21e7626e0d0166a
Source dataset
uspto-grants-2012_08
Patent number
US08247573B2

Reaction notes

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