Triethylamine → 3-(4-Cyanophenyl)-N-{3-[(2,3-dichlorobenzenesulphonyl)methyl-amino]propyl}propionamide

HRID 1591748Notes

Reaction equation

HRID 1591748 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1)#[N:2].[CH3:14][N:15]([C:17]([O:21]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([N:38]([CH2:41][CH3:42])[CH2:39]C)C.NCCCN(C)[S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[C:52]=1[Cl:58])(=[O:50])=[O:49]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:13][C:17]([NH:15][CH2:14][CH2:42][CH2:41][NH:38][CH2:39][S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[C:52]=2[Cl:58])(=[O:49])=[O:50])=[O:21])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 225698632-(4-Cyanophenyl)propanoic acidHCID 69423487N-(3-aminopropyl)-2,3-dichloro-N-methylbenzenesulphonamide

Product 1

HCID 694217413-(4-Cyanophenyl)-N-{3-[(2,3-dichlorobenzenesulphonyl)methyl-amino]propyl}propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.47 g (8.41 mmol) of 4-cyanophenylpropionic acid, 3.1 g (9.65 mmol) of TBTU and 5.0 ml of triethylamine in 150 ml of tetrahydrofuran was stirred at room temperature for 30 minutes, 2.5 g (8.41 mmol) of N-(3-aminopropyl)-2,3-dichloro-N-methylbenzenesulphonamide were than added and the mixture was stirred overnight. The mixture was evaporated to dryness, potassium carbonate solution (10%) was added to the residue and the mixture was extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, drive over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography (mobile phase: dichloromethane/methanol 150:1 to 100:1).

Workup

  1. additionthan added
  2. customThe mixture was evaporated to dryness, potassium carbonate solution (10%)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water and saturated sodium chloride solution, drive over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ef57e68456c4b97a671b3306a2a44c1
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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