Triethylamine → N-(5-Ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamide

HRID 968282ノート

反応式

HRID 968282 の反応式
Cl.CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[NH2:13][C:14]1[CH:27]=[C:26]2[C:17]([C:18](=[O:30])[N:19]([CH2:28][CH3:29])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)=[CH:16][CH:15]=1.[OH:31]N1C2C=CC=CC=2N=N1.C([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C>ClCCl.C(OCC)(=O)C>[CH2:28]([N:19]1[C:18](=[O:30])[C:17]2[C:26](=[CH:27][C:14]([NH:13][C:4](=[O:31])[CH2:5][C:6]3[CH:45]=[CH:44][N:43]=[CH:46][CH:47]=3)=[CH:15][CH:16]=2)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]1=2)[CH3:29]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103993089-amino-5-ethyl-5H-phenanthridin-6-one

生成物 1

HCID 10247746N-(5-Ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamide収率 34%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (962 mg, 5.03 mmol) was added in one portion to a solution of 9-amino-5-ethyl-5H-phenanthridin-6-one 1A (1.0 g, 4.2 mmol), 1-hydroxybenzotriazole (850 mg, 6.3 mmol), and triethylamine (0.64 ml, 4.6 mmol) in dichloromethane (20 ml). The resultant solution was stirred at 23° C. for 16 hours and diluted with ethyl acetate (50 ml). The reaction mixture was washed with water (25 ml) and saturated aqueous ammonium chloride (25 ml) and dried over anhydrous magnesium sulfate and concentrated. The solid residue was triturated with methanol to provide N-(5-ethyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-2-pyridin-4-yl-acetamide 5A (509 mg, 34%).

後処理

  1. washThe reaction mixture was washed with water (25 ml) and saturated aqueous ammonium chloride (25 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe solid residue was triturated with methanol

出典と根拠

ORDレコード
ord-c1c974728dc24fe3b2823898ff0d555f
出典データセット
uspto-grants-2005_10
特許番号
US06958347B2

反応ノート

読み込み中…