Hexane → HCID 46917514, compound

HRID 888264Notes

Reaction equation

HRID 888264 reaction equation
C([O-])(O)=O.[Na+].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][C:12](Cl)=[O:13].[C:15]1([S:21][CH2:22][CH2:23][S:24][C:25]2[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCCCCC>O1CCOCC1>[C:15]1([S:21][CH2:22][CH2:23][S:24][C:25]2[C:30]([NH:31][C:12](=[O:13])[CH2:11][C:7]3[S:6][CH:10]=[CH:9][CH:8]=3)=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 67133588HCID 67133588, compound

Product 1

HCID 46917514HCID 46917514, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

420 mg (5.0 mmol) NaHCO3 and 402 mg (2.5 mmol) 2-(thiophen-2-yl)acetic acid chloride were added to a solution of 262 mg (1.0 mmol) [2-(2-phenylsulfanyl-ethylsulfanyl)-pyridin-3-yl]amine (VPF-006) in dioxane (25 ml) at 0° C. and then the mixture was stirred for 16 h at RT. Then it was diluted with EE and washed with water and brine. The organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 186 mg (0.5 mmol, 48%) N-[2-(2-phenylsulfanyl-ethylsulfanyl)-pyridin-3-yl]-2-thiophen-2-yl acetamide. MS: m/z 387.1 [M+H]+.

Workup

  1. additionThen it was diluted with EE
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-5547b07f466748f3873753715499632a
Source dataset
uspto-grants-2012_08
Patent number
US08247573B2

Reaction notes

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