Pyridine → 2-[(S)-1-Phenylethylamino]-4-[5-(pyridin-2-yl)-benzimidazol-1-yl]pyrimidine

HRID 2300846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300846
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23](N)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=O.[Na+].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([Cu])#N>C(O)(=O)C.O.C(OCC)(=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 98839772-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 98006882-[(S)-1-Phenylethylamino]-4-[5-(pyridin-2-yl)-benzimidazol-1-yl]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 37 mg of 2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) in acetic acid (1.0 mL) was added NaNO2 (7.7 mg) in H2O (0.5 mL). The mixture was stirred 1 h at 0° C. Pyridine (1 mL) was added followed by CuCN (9.8 mg). Gas evolution was observed. The reaction mixture was poured into ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated. The product mixture was purified by silica gel chromatography eluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound. Mass spectrum (ESI): 293.3 (M+1).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product mixture was purified by silica gel chromatography
  6. washeluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-b7826af564db407181a16c8a6cc47c9a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498165B1

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