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

HRID 610776

反応式

HRID 610776 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e3dedee516d44c37a0e50c81c92f8e2e
出典データセット
uspto-grants-1999_12
特許番号
US05998666

関連ノート

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