Triethylamine → 2-Chloro-5-(6-methyl-pyridin-3-yl)-N-(1-p-tolyl-cyclohexylmethyl)-benzamide

HRID 1988367ノート

反応式

HRID 1988367 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:40]1([CH3:54])[CH:45]=[CH:44][C:43]([C:46]2([CH2:52][NH2:53])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([NH:53][CH2:52][C:46]1([C:43]2[CH:42]=[CH:41][C:40]([CH3:54])=[CH:45][CH:44]=2)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)=[O:6]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184386612-Chloro-5-(6-methylpyridin-3-yl)benzoic acidHCID 184387081-[1-(4-Methylphenyl)cyclohexyl]methanamine

生成物 1

HCID 588181732-Chloro-5-(6-methyl-pyridin-3-yl)-N-(1-p-tolyl-cyclohexylmethyl)-benzamide収率 27.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid (73 mg, 0.29 mmol) in N,N-dimethylformamide (4 mL) was added sequentially, stirring at room temperature for 10 minutes after each addition, 1-hydroxybenzotriazole (48 mg, 0.35 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg, 0.32 mmol), C-(1-p-tolyl-cyclohexyl)-methylamine (60 mg, 0.29 mmol) and triethylamine (31 mg, 0.31 mmol). The mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase chromatography to afford the title compound (35 mg). LCMS (m/z) 433.2 M+1.

後処理

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase chromatography

出典と根拠

ORDレコード
ord-ce40cefca7a741209859a2c29031745e
出典データセット
uspto-grants-2009_06
特許番号
US07553972B2

反応ノート

読み込み中…