Potassium Carbonate → N-cycloheptyl-5-[benzyl{2-(3-(aminocarbonylamino)phenoxy)ethyl}amino]pentanamide

HRID 610776

Reaction equation

HRID 610776 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]([NH2:17])=[O:16])[CH:11]=[CH:12][CH:13]=1.[CH:18]1([NH:25][C:26](=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][N:31]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:32][CH2:33]Cl)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[CH:18]1([NH:25][C:26](=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][N:31]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:32][CH2:33][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([NH2:17])=[O:16])[CH:9]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12796m-HydroxyphenylureaHCID 22125964N-cycloheptyl-5-[benzyl(2-chloroethyl)amino]pentanamide

Product 1

HCID 22125977N-cycloheptyl-5-[benzyl{2-(3-(aminocarbonylamino)phenoxy)ethyl}amino]pentanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

Potassium carbonate (0.92 g, 6.6 mmole) is added to a solution of 3-hydroxyphenylurea (1 g, 6.6 mmole) in dimethylformamide (20 ml) and said mixture is stirred for 10 minutes at 20° C. A solution of N-cycloheptyl-5-[benzyl-(2-chloroethyl)amino]pentanamide (2.21 g, 6 mmole) in dimethylformamide (20 ml) is then added dropwise, the mixture being kept under agitation for 4 hours at 80° C. The solvent is evaporated under reduced pressure, then the residue is taken up in dichloromethane (50 ml) and washed with water. The organic phase is collected and dried then, after evaporation of the solvent, the desired compound is obtained in the form of an oil. It is purified by flash chromatography over silica gel in a mixture of dichloromethane/methanol (95/5) to give 1.75 g (60%) of pure compound. NMR-1H (CDCl3),;1.30-1.90 (m, 16H), 2.12 (t, 2H, J=6 Hz), 2.53 (t, 2H, J=6 Hz), 2.80 (t, 2H, J=6 Hz), 3.63 (s, 2H), 3.95 (m, 1H), 4.07 (t, 2H, J=6 Hz), 4.93 (s, 1H), 5.55 (m, 1H), 6.68 (m, 2H), 7.19 -7.30 (m, 9H).

Workup

  1. waitthe mixture being kept under agitation for 4 hours at 80° C
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic phase is collected
  5. customdried
  6. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-e3dedee516d44c37a0e50c81c92f8e2e
Source dataset
uspto-grants-1999_12
Patent number
US05998666

Linked notes

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