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Sodium Iodide → 3-(4-acetylpiperazin-1-yl)propoxyl-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine

HRID 1785178
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Reaktionsgleichung

Reaktionsgleichung von HRID 1785178
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23](OCCCCl)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[C:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])[CH3:35].[I-].[Na+]>COCCO.ClCCl>[C:34]([N:37]1[CH2:42][CH2:41][N:40]([CH2:3][CH2:4][CH2:5][O:6][C:19]2[N:18]=[C:17]([NH:16][C:3]3[C:4]4[O:8][CH2:7][O:6][C:5]=4[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])=[CH:10][C:2]=3[Cl:1])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=2)[CH2:39][CH2:38]1)(=[O:36])[CH3:35]
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Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 837951-AcetylpiperazineHCID 68882624N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine

Produkt 1

HCID 866015663-(4-acetylpiperazin-1-yl)propoxyl-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amineAusbeute 145 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.158 g) was dissolved in 2-methoxyethanol (5 ml) and then N-acetylpiperazine (0.600 g) was added and the mixture heated to 105° C. A small amount of sodium iodide was added to the reaction mixture, and heating continued for a total of 2½ hours. The reaction mixture was cooled to room temperature and then diluted with dichloromethane. The mixture was washed with a water/brine (5/1) mixture followed by brine and then dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of dichloromethane and methanol as eluent. There was thus obtained the title compound (0.136 g) as a pale yellow foam. NMR Spectrum: (CDCl3) 2.10 (quin, 2H), 2.43 (m, 2H), 2.47 (m, 2H), 2.57 (t, 2H), 3.46 (s, 3H), 3.47 (m, 2H), 3.49 (s, 3H), 3.62 (t, 3H), 3.98 (s, 3H), 4.25 (t, 2H), 4.35 (s, 2H), 6.08 (s, 2H), 7.06 (s, 1H), 7.20 (s, 1H), 7.28 (s, 2H), 8.62 (s, 1H); Mass Spectrum: M+H+ 582/584.

Aufarbeitung

  1. temperatureheating
  2. customcontinued for a total of 2½ hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe mixture was washed with a water/brine (5/1) mixture
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica using
  8. temperatureincreasingly polar mixtures of dichloromethane and methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2467d81877434cfe8187954255027fdb
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07504408B2

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