Dimethyl Sulfoxide → HCID 24780778, compound

HRID 2403545Notes

Reaction equation

HRID 2403545 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([CH2:13][C:14]([NH:16][CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([OH:39])[CH3:38])[CH:32]=3)[CH2:27][CH2:26]2)[CH2:19][CH2:18]1)=[O:15])#[N:12].C(N(CC)CC)C>ClCCl.O>[C:37]([C:33]1[CH:32]=[C:31]([N:28]2[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH:20]3[CH2:21][CH2:22][CH:17]([NH:16][C:14](=[O:15])[CH2:13][C:11]#[N:12])[CH2:18][CH2:19]3)[CH2:30][CH2:29]2)[CH:36]=[CH:35][CH:34]=1)(=[O:39])[CH3:38]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57964620HCID 57964620, compound

Product 1

HCID 24780778HCID 24780778, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 44 mg (0.35 mmol) of oxalyl chloride in 1 mL of dichloromethane is purged with argon and cooled to a temperature close to −70° C. A solution of 66 mg (0.8 mmol) of dimethyl sulfoxide in 1 mL of dichloromethane is added. Stirring is maintained at a temperature close to −70° C. for 15 minutes and a solution of 120 mg (0.3 mmol) of 2-cyano-N-[4-(2-{4-[3-(1-hydroxyethyl)phenyl]piperazin-1-yl}ethyl)cyclohexyl]acetamide trans/cis 80/20 in 4 mL of dichloromethane is added. After an additional stirring for 15 minutes at a temperature close to −70° C., 110 mg (1.08 mmol) of triethylamine are added. The mixture is allowed to warm to room temperature then stirred overnight at room temperature. The mixture is poured into water and extracted twice with ethyl acetate. The organic phases are combined, washed with water, then brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The oily residue is purified over 5 g silica gel (eluant dichloromethane/methanol 98/2 then 95/5). To give 25 mg (21%) of N-(4-{2-[4-(3-acetylphenyl)piperazin-1-yl]ethyl}cyclohexyl)-2-cyanoacetamide trans/cis 80/20 as a white solid.

Workup

  1. temperaturecooled to a temperature
  2. customclose to −70° C
  3. temperatureis maintained at a temperature
  4. customclose to −70° C. for 15 minutes
  5. stirringAfter an additional stirring for 15 minutes at a temperature
  6. customclose to −70° C.
  7. stirringthen stirred overnight at room temperature
  8. extractionextracted twice with ethyl acetate
  9. washwashed with water
  10. dry with materialbrine, dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe oily residue is purified over 5 g silica gel (eluant dichloromethane/methanol 98/2

Sources & evidence

ORD record
ord-49d948b6813c4a4c9fd395bae2287485
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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