4-Cyanopyridine → 2-phenyl-5-(2-(pyridin-4-yl)-1H-imidazol-5-yl)pyrimidine

HRID 42284

Reaktionsgleichung

Reaktionsgleichung von HRID 42284
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.C(C1C=CN=CC=1)#N.[CH2:27]([N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)C1C=CC=CC=1.B(O)(O)C1C=CC=C(F)C=1>ClCCl.CO>[C:39]1([C:35]2[N:34]=[CH:27][C:38]([C:12]3[NH:8][C:9]([C:13]4[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=4)=[N:10][CH:11]=3)=[CH:37][N:36]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Komponenten

6

Edukt 4

HCID 75064-CyanopyridineHCID 27339863-Fluorophenylboronic acidHCID 30159391-benzyl-2-phenyl-1H-imidazoleHCID 684114624-(1-benzyl-1H-imidazol-2-yl)pyridine

Produkt 1

HCID 451375622-phenyl-5-(2-(pyridin-4-yl)-1H-imidazol-5-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

The title compound was prepared by the method described in Example 1, except that 4-(1-benzyl-1H-imidazol-2-yl)pyridine (prepared according to Example 8, Step A, except that commercially available 4-cyanopyridine was used instead of 3-fluorobenzonitrile) was used in place of the 1-benzyl-2-phenyl-1H-imidazole in Step C; Rf 0.26 with 95:5 v/v dichloromethane-methanol; melting point 300° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.40 (s, 2H), 8.73 (d, 2H), 8.50-8.45 (m, 2H), 8.25 (bs, 1H), 8.00 (d, 2H), 7.62-7.55 (m, 4H); MS (ESI+) m/z 300.0 (M+1); H-PGDS FPBA IC50: 0.125 μM; H-PGDS inhibitor EIA IC50: 0.075 μM.

Aufarbeitung

  1. customprepared

Quellen und Nachweise

ORD-Eintrag
ord-e45afdb3171f4f8893d56f5e71307c2c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536185B2

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