Dimethyl Sulfoxide → HCID 59438442, compound

HRID 2177543Notes

Reaction equation

HRID 2177543 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([S:43][CH3:44])[C:14]=1[C:15]([NH:17][C:18]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH:22]([O:24]COC)[CH2:21][N:20]([CH3:28])[CH2:19]1)=[O:16].C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]1[CH:38]=[C:37]([C:39]([F:42])([F:40])[F:41])[CH:36]=[C:35]([S:43][CH3:44])[C:14]=1[C:15]([NH:17][C:18]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:23][C:22](=[O:24])[CH2:21][N:20]([CH3:28])[CH2:19]1)=[O:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59438419HCID 59438419, compound

Product 1

HCID 59438442HCID 59438442, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a −50° C. solution of 11 ul (0.21 mmol) oxalyl chloride in 0.8 ml dichloromethane was added a solution of 17.2 ul DMSO in 0.2 ml dichloromethane over a period of 15 minutes. The reaction mixture was stirred for 10 minutes, after which a solution of 50 mg (0.11 mmol) rac-N-(5-hydroxy-1-methyl-3-phenyl-piperidin-3-yl)-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide (example 51) in 0.8 ml dichloromethane was added over a period of 15 minutes. After 30 min stirring, 77 ul (0.55 mmol) triethylamine was added. The reaction mixture was stirred for 15 minutes, then allowed to warm to room temperature and quenched with water and the aqueous layer was extracted with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 15%) to provide 44 mg (89%) of the title compound as a white foam. MS (m/e): 453.1 (MH+).

Workup

  1. stirringAfter 30 min stirring
  2. stirringThe reaction mixture was stirred for 15 minutes
  3. customquenched with water
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 15%)

Sources & evidence

ORD record
ord-0f05e3bfacee4964880b57b8da11b7bd
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

Loading…