Cyclohexaneacetic acid → HCID 67134013, compound

HRID 222551Notes

Reaction equation

HRID 222551 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]1([CH2:13][C:14]([OH:16])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([O-])(O)=O.[Na+].[CH2:22]([S:24][C:25]1[C:34]([NH2:35])=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1)[CH3:23]>C(Cl)Cl.CC(=O)OCC.CCCCCC.CC(=O)OCC.CN(C=O)C>[CH:7]1([CH2:13][C:14]([NH:35][C:34]2[C:25]([S:24][CH2:22][CH3:23])=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

9

Reactant 4

HCID 21363Cyclohexaneacetic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 67133831HCID 67133831, compound

Product 1

HCID 67134013HCID 67134013, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

760 mg (6 mmol) of oxalyl chloride and a catalytic amount of DMF (100 μl) were added at 0° C. to a suspension of 427 mg (3 mmol) of 2-cyclohexylacetic acid in DCM (45 ml). After stirring for 4 h at RT, the mixture was concentrated in vacuo. The residue was taken up in dioxane (30 ml), and 670 mg (8 mmol) of NaHCO3 were added. After stirring for 5 min at RT, 408 mg (2 mmol) of 2-(ethylthio)quinolin-3-amine (VC04) were added. After stirring for 16 h at RT, the reaction solution was diluted with EA and washed with a sat. aq. NaHCO3 soln. and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 19:1) of the residue yielded 397 mg (1.0 mmol, 51%) of 2-cyclohexyl-N-(2-ethylsulfanyl-quinolin-3-yl)-acetamide. MS: m/z 329.2 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. stirringAfter stirring for 5 min at RT
  3. stirringAfter stirring for 16 h at RT
  4. washwashed with a sat. aq. NaHCO3 soln
  5. dry with materialand brine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b680138b8da466eb6ffcc4a30977185
Source dataset
uspto-grants-2012_06
Patent number
US08207342B2

Reaction notes

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