Triethylamine → 10H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amide

HRID 12262

반응식

HRID 12262 반응식
[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]([CH3:26])[CH2:23][CH2:24][NH2:25].C(N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 1010675710H-Indolo[3,2-b]quinoline-11-carboxylic acid

생성물 1

HCID 1147303410H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amide수율 61%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

실험 절차

10H-indolo[3,2-b]quinoline-11-carboxylic acid (0.5 g, 1.9 mmol) was dissolved in 20 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-dimethylethylendiamine (0.2 mL, 2.26 mmol) and triethylamine (2.2 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 (0.38 g, 61%) as a solid. m. p. 175-176° 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)j. MS (EI, m/z) 277 (M++1).

후처리

  1. customwas 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)

출처 및 근거

ORD 기록
ord-5ef6c1c4b096459d8233747f623d138d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728000B2

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