1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-N-(methylsulfonyl)-4-oxobutanamide

HRID 534916Notes

Reaction equation

HRID 534916 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:23])[CH2:18][CH2:19][C:20](O)=[O:21])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:23])[CH2:18][CH2:19][C:20]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:21])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66750856HCID 66750856, compound

Product 1

HCID 667512384-(4-(2-tert-butylphenyl)piperazin-1-yl)-N-(methylsulfonyl)-4-oxobutanamideYield 41.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-4-oxobutanoic acid obtained in Example 53 (0.100 g, 0.31 mmol), EDCI (0.090 g, 0.47 mmol), HOBt (0.064 g, 0.47 mmol) and diisopropylethylamine (0.163 g, 1.26 mmol) in methylene chloride (2.0 mL) was added methane-sulfonamide (0.031 g, 0.31 mmol) at room temperature. After 18 h the reaction mixture was diluted with ethyl acetate, washed with 1.0 M hydrochloric acid (5.0 mL), water (5.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 95:5 methylene chloride/MeOH) to provide 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-N-(methylsulfonyl)-4-oxobutanamide (0.051 g, 41%) as an off-white solid, mp: 89-90° C.

Workup

  1. washwashed with 1.0 M hydrochloric acid (5.0 mL), water (5.0 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, 95:5 methylene chloride/MeOH)

Sources & evidence

ORD record
ord-ad407cd282314b79989b8436f247e955
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…