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

HRID 610776

반응식

HRID 610776 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3dedee516d44c37a0e50c81c92f8e2e
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998666

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