4-Phenoxyphenyl isocyanate → 1-[2-(3,3-dimethoxypropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea

HRID 1825839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825839
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH2:15])[CH:11]=[CH:12]2)=[N:7]1.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH:15][C:32]([NH:31][C:28]3[CH:29]=[CH:30][C:25]([O:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:26][CH:27]=3)=[O:33])[CH:11]=[CH:12]2)=[N:7]1

Komponenten

4

Edukt 2

HCID 27348964-Phenoxyphenyl isocyanateHCID 221389282-(3,3-dimethoxypropyl)-2H-indazole-6-ylamine

Produkt 1

HCID 221388991-[2-(3,3-dimethoxypropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(3,3-dimethoxypropyl)-2H-indazole-6-ylamine (582 mg, 2.48 mmol) in THF (9 mL) was added 4-phenoxyphenylisocyanate (523 mg, 2.48 mmol) and the reaction was heated to 40 C for 3 h. The heating bath was removed and the reaction was then concentrated under reduced pressure to a dark oil. The oil was dissolved in Ethyl acetate and passed through a small plug of SiO2 gel, eluting with additional EtOAc. The eluent was concentrated under reduced pressure to give 1-[2-(3,3-dimethoxypropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea as a beige solid. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.50 (m, 2 H), 3.32 (m, 6 H), 4.36 (m, 3 H), 6.97 (m, 6 H), 7.09 (t, J=7.46 Hz, 1 H), 7.36 (m, 2 H), 7.48 (m, 2 H), 7.59 (d, J=8.82 Hz, 1 H), 7.83 (s, 1 H) and 8.66 (m, 2 H); MS(ESI) 445 (M−H)−.

Aufarbeitung

  1. temperaturethe reaction was heated to 40 C for 3 h
  2. customThe heating bath was removed
  3. concentrationthe reaction was then concentrated under reduced pressure to a dark oil
  4. dissolutionThe oil was dissolved in Ethyl acetate
  5. washeluting with additional EtOAc
  6. concentrationThe eluent was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9d0f1b33cd71445a9577687205bb2869
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049307B2

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