2,4-Dimethoxybenzylamine → 1-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

HRID 871004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871004
Cl[C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[F:26])=[O:17])=[CH:11][CH:10]=2)[S:4][N:3]=1.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>C(Cl)Cl>[C:7]([C:6]1[C:2]([NH:32][CH2:31][C:30]2[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:29]=2[O:28][CH3:27])=[N:3][S:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[F:26])=[O:17])=[CH:11][CH:10]=1)#[N:8]

Komponenten

4

Edukt 2

HCID 5972502,4-DimethoxybenzylamineHCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea

Produkt 1

HCID 866892251-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)ureaAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
73 °C

Versuchsvorschrift

A suspension of 1-[4-(3-chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea (4.3 g, 11.1 mmol) in 15 mL of 2,4-dimethoxybenzylamine was heated to 73° C. for 24 h. The reaction became clear after ˜3 h. The reaction was cooled to RT. The residue was diluted with 300 mL of DCM and was washed with 10% HCl solution two times, saturated Na2S2O5 two times followed by brine. The organic solution was dried with MgSO4, filtered, and concentrated. The crude product was purified by flash silica gel column eluted with 2-5% MTBE in DCM/hexanes (2:1) to obtain the title compound as a light yellow solid (1.19 g, 21%).

Aufarbeitung

  1. temperatureThe reaction was cooled to RT
  2. washwas washed with 10% HCl solution two times, saturated Na2S2O5 two times
  3. dry with materialThe organic solution was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash silica gel column
  7. washeluted with 2-5% MTBE in DCM/hexanes (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-044bc3cb43a74d2ca08e601ee66cd699
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969583B2

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