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1H-Indazole → (4-Chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amine

HRID 1514349
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514349
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:16])[N:3]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[N:18]1>C(#N)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:16])[N:3]=[C:2]([N:18]3[CH:19]=[C:20]4[C:25]([CH:24]=[CH:23][CH:22]=[CH:21]4)=[N:17]3)[N:7]=2)=[CH:10][CH:11]=1.[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:16])[N:3]=[C:2]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[N:18]3)[N:7]=2)=[CH:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 92211H-IndazoleHCID 58026187(2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine

Produkt 2

HCID 24764453(4-Chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amineAusbeute 14 %HCID 24825861(4-Chloro-phenyl)-(2-indazol-1-yl-6-methyl-pyrimidin-4-yl)-amineAusbeute 5,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

(2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine (300 mg, 1.18 mmol) was dissolved in acetonitrile (4 mL), indazole (150 mg, 1.3 mmol) was added and the mixture was heated in a microwave oven at 160° C. for 30 minutes. The solvent was removed in vacuo and the remaining residue was basified with aqueous sodium hydrogencarbonate and extracted with chloroform. The combined organic phases were dried with sodium sulphate, filtrated and evaporated. The crude product was purified by column chromatography with ethyl acetate-hexane as eluent to give (4-chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amine (56 mg, 14%, mp=224.7-226.7° C.) (LC-ESI-HRMS of [M+H]+ shows 336.1019 Da. Calc. 336.101598 Da, dev. 0.9 ppm) as a white solid and (4-chloro-phenyl)-(2-indazol-1-yl-6-methyl-pyrimidin-4-yl)-amine (21 mg, 5.3%, mp=166.7-168.7° C.) (LC-ESI-HRMS of [M+H]+ shows 336.1007 Da. Calc. 336.101598 Da, dev. −2.7 ppm) as a white solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic phases were dried with sodium sulphate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude product was purified by column chromatography with ethyl acetate-hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-31488919fec946ebb872a34974a54076
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222262B2

Notizen zur Reaktion

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