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Phosgene → N-(4-isopropylbenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

HRID 586011
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 586011
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:12](Cl)(Cl)=[O:13].CCN(C(C)C)C(C)C.[NH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]=[C:29]([CH3:36])[N:30]=[CH:31]2>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:12]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:27]=2[CH:28]=[C:29]([CH3:36])[N:30]=[CH:31]3)=[O:13])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]
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Komponenten

6

Edukt 4

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 1382214-IsopropylbenzylamineHCID 122120553-Methylisoquinolin-5-amine

Produkt 1

HCID 22032671N-(4-isopropylbenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel
2×

Versuchsvorschrift

4-Isopropylbenzylamine (748 mg, 5.02 mmol) in toluene (20 mL) was refluxed with 20% w/v phosgene solution in toluene (3 mL) overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in toluene (20 mL) and was treated with DIEA (4 mL) and 5-amino-3-methylisoquinoline (500 mg, 3.16 mmol). The reaction mixture was stirred was at 80° C. for 6 hours. After cooling to room temperature, a precipitate formed which was collected by filtration and purified by silica gel chromatography (98:2 CH2Cl2:CH3OH) to provide the title compound. The corresponding hydrochloride salt was formed by treatment with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.16 (s, 1H), 8.60 (s, 1H), 8.24 (dd, 1H, J=7.5 Hz, 1.0 Hz), 7.74 (s, 1H), 7.68 (d, 1H, J=8.2 Hz), 7.50 (t, 1H, J=8.0 Hz), 7.22-7.30 (m, 4H), 6.99 (t, 1H, 5.6 Hz), 4.32 (d, 2H, J=7.8 Hz), 2.88 (m, 1H), 2.64 (s, 3H), 1.20 (d, 6H, J=6.8 Hz); MS (ESI+) m/z 334 (M+H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. temperatureAfter cooling to room temperature
  3. customa precipitate formed which
  4. filtrationwas collected by filtration
  5. custompurified by silica gel chromatography (98:2 CH2Cl2:CH3OH)

Quellen und Nachweise

ORD-Eintrag
ord-c8a6c76255054074b983e802c6f74392
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06933311B2

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