Acetic Acid → N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-N4-(5-isopropyl-2-methylphenyl)-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine

HRID 451197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451197
Cl[C:2]1[N:3]=[C:4]([NH:17][CH3:18])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[Cl:19][C:20]1[N:21]=[CH:22][N:23]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=2[O:32][CH3:33])[CH:24]=1.[CH3:34][C:35](O)=O.[OH-].[Na+]>O1CCOCC1>[Cl:19][C:20]1[N:21]=[CH:22][N:23]([C:25]2[CH:31]=[CH:30][C:28]([NH:29][C:2]3[N:3]=[C:4]([NH:17][C:18]4[CH:9]=[C:8]([CH:11]([CH3:16])[CH3:12])[CH:6]=[CH:5][C:35]=4[CH3:34])[C:5]4[CH2:10][CH2:9][CH:8]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[C:6]=4[N:7]=3)=[CH:27][C:26]=2[O:32][CH3:33])[CH:24]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 580752952-chloro-N-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amineHCID 580757574-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline

Produkt 1

HCID 58075604N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-N4-(5-isopropyl-2-methylphenyl)-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-N-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation Gp) (26.0 mg, 100 μmol) in Dioxane (Ratio: 1, Volume: 175 μl) was added 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline (Preparation A) (22.37 mg, 100 μmol) and AcOH (Ratio: 1.000, Volume: 175 μl). The resulting mixture was brought to 100° C. and stirred overnight. The reaction mixture was brought to pH 10 by the addition of 1 N aqueous NaOH. The resulting mixture was extracted with EtOAc (3×4 mL). The combined organic extracts were washed with brine (4 mL), dried over MgSO4, filtered and concentrated in vacuo. The product was purified by Prep HPLC to yield the title compound. LC-MS (M+H)+=565.2.

Aufarbeitung

  1. customwas brought to 100° C.
  2. extractionThe resulting mixture was extracted with EtOAc (3×4 mL)
  3. washThe combined organic extracts were washed with brine (4 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f689d02450574a7398c29464dd2ec828
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486952B2

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