Triethylamine → 10h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amide

HRID 12263

反応式

HRID 12263 の反応式
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([C:18]([OH:20])=O)=[C:4]1[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:5]1=[N:6]2.[CH3:21][N:22]([CH3:27])[CH2:23][CH:24]([NH2:26])C.[CH2:28](N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl>[CH3:21][N:22]([CH3:27])[CH:23]([CH3:28])[CH2:24][NH:26][C:18]([C:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[N:6]=[C:5]2[C:11]3[C:16]([NH:17][C:4]=12)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 1010675710H-Indolo[3,2-b]quinoline-11-carboxylic acid

生成物 1

HCID 1145084410h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amide収率 31%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

10H-Indolo[3,2-b]quinoline-11-carboxylic acid (0.2 g, 0.76 mmol) was dissolved in 8 ml of refluxing SOCl2. After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylproylendiamine (0.1 mL, 0.97 mmol) and triethylamine (1 ml) in 10 ml of CH2Cl2 was added at room temperature, and the mixture was stirred for 14 hours. The organic phase was washed (NaHCO3, brine) and dried (MgSO4). Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10) yielded the desired compound (80 mg, 31%) as a solid. m. p. 188-189° C. 1H-NMR [MeOD,_, ppm]: 8.16 (d, J=7.8 Hz, 1H), 7.92 (m, 2H), 7.35-7.20 (m, 3H), 7.04 (m, 2H), 3.62 (m, 2H, CH2NO), 2.55 (m, 2H, CH2N(CH3)2), 2.29 (s, 6H, N(CH3)2), 1.88 (m, 2H, CHO. MS (EI, m/z) 347 (M++1).

後処理

  1. customAfter 6 hours a clear solution was obtained
  2. customall volatiles were removed in vacuo
  3. washThe organic phase was washed (NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

出典と根拠

ORDレコード
ord-35de871dc825411f82857dabd9c55ffb
出典データセット
uspto-grants-2010_06
特許番号
US07728000B2

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