Diisopropylethylamine → 3-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-nitro-1H-indole

HRID 53146

反応式

HRID 53146 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15]Br)([O-:3])=[O:2].[CH3:17][O:18][C:19]1[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:21][CH:22]=[N:23][CH:24]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:20]([N:25]2[CH2:30][CH2:29][N:28]([CH2:15][CH2:14][CH2:13][C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[NH:9][CH:8]=3)[CH2:27][CH2:26]2)=[N:21][CH:22]=[N:23][CH:24]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 104201525-Methoxy-4-(piperazin-1-yl)pyrimidineHCID 199620433-(3-Bromopropyl)-5-nitro-1H-indole

生成物 1

HCID 199620393-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-nitro-1H-indole収率 70%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-nitro-3-(3-bromopropyl)indole (0.57 g, 2.0 mmol), 1-(5-methoxy-4-pyrimidyl)piperazine, (0.47 g, 2.4 mmol), KI (0.40 g, 2.4 mmol) and diisopropylethylamine (1.75 mL, 10.0 mmol) in 20 mL of acetonitrile was heated to reflux under Ar for 6 h. The cooled reaction mixture was diluted with ethyl acetate and washed (H2O, brine). The aqueous phase was back-extracted with dichloromethane and the combined organic phase was washed (H2O, brine), dried (Na2SO4) and evaporated. The resulting residue was chromatographed (SiO2 /CH2Cl2 -MeOH, 95:5) to give a solid which was triturated with dichloromethane-hexane to afford the title compound (0.55 g, 70%) as a yellow solid, mp 163°-166° C.: IR (KBr) 3440, 3175, 1578, 1320 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ8.60 (d, J=2.1 Hz, 1H), 8.47 (br s, 1H), 8.33(s, 1H), 8.11 (dd, J=9.0, 2.2 Hz, 1H), 7.89 (s, 1H), 7.38 (d, J=9.0 Hz, 1H), 7.18 (d, J=2.0 Hz, 1H), 3.86 (s, 3H), 3.8-3.9 (m, 4H), 2.86 (t, J=7.4 Hz, 2H), 2.59 (t, J=4.9 Hz, 4H), 2.50 (t, J=7.5 Hz, 2H), 2.05-1.90 (m, 2H). Anal. Calcd for C20H24N6O3. H2O. 0.1 CH2Cl2 : C, 57.08; H, 6.24; N, 19.87. Found: C, 57.37; H, 5.85; N, 19.53.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under Ar for 6 h
  3. customThe cooled reaction mixture
  4. washwashed (H2O, brine)
  5. extractionThe aqueous phase was back-extracted with dichloromethane
  6. washthe combined organic phase was washed (H2O, brine)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe resulting residue was chromatographed (SiO2 /CH2Cl2 -MeOH, 95:5)
  10. customto give a solid which
  11. customwas triturated with dichloromethane-hexane

出典と根拠

ORDレコード
ord-0654ffa8cf6349d7b041fe7b0f90abf0
出典データセット
uspto-grants-1997_04
特許番号
US05618816

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