1,2-Dichloroethane → n-Cycloheptyl-2-(5,5-dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2(r,s)-yl)acetamide

HRID 747047Notes

Reaction equation

HRID 747047 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][N:6]([S:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])(=[O:10])=[O:9])[CH:5]([CH2:20][C:21](O)=[O:22])[C:4](=[O:24])[NH:3]1.[CH:26]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)CCl.CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH:26]1([NH:33][C:21](=[O:22])[CH2:20][CH:5]2[C:4](=[O:24])[NH:3][C:2]([CH3:1])([CH3:25])[CH2:7][N:6]2[S:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])(=[O:9])=[O:10])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 2899CycloheptylamineHCID 8857Ethyl AcetateHCID 69078569(5,5-Dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid

Product 1

HCID 11751607n-Cycloheptyl-2-(5,5-dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2(r,s)-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To (5,5-dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid (0.32 g, 0.94 mmol) in DMF (3 mL) was added cycloheptyl amine (0.5 mL), EDC (0.5 g, 2.5 mmol), and DMAP (0.3 g, 2.6 mmol). The mixture was stirred at RT overnight. TLC indicated that the reaction was not complete. Additional EDC (0.3 g) was added and the mixture was heated at 65° C. for 1 h. The mixture was cooled to RT. EtOAc (80 mL) was added and mixture was washed with dilute HCl in brine. The EtOAc solution was dried and evaporated to give the crude compound. Column chromatograph purification (silica gel, 0-2% MeOH/CH2Cl2) gave the titled compound. MS: 464.1 (M+1)+.

Workup

  1. temperaturethe mixture was heated at 65° C. for 1 h
  2. temperatureThe mixture was cooled to RT
  3. washmixture was washed with dilute HCl in brine
  4. dry with materialThe EtOAc solution was dried
  5. customevaporated
  6. customto give the crude compound
  7. customColumn chromatograph purification (silica gel, 0-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2e9773d9906441bdbf2c66a05e69db29
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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