Pyridine-2-carbonitrile → 2-phenyl-5-(2-(pyridin-2-yl)-1H-imidazol-5-yl)pyrimidine

HRID 42280

Reaction equation

HRID 42280 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)C1C=CC=CC=1.C(C1C=CC=CN=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:18]=[CH:17][CH:16]=[CH:15][N:14]=4)=[N:10][CH:11]=3)=[CH:37][N:36]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7522Pyridine-2-carbonitrileHCID 27339863-Fluorophenylboronic acidHCID 30159391-benzyl-2-phenyl-1H-imidazoleHCID 684110012-(1-benzyl-1H-imidazol-2-yl)pyridine

Product 1

HCID 592523992-phenyl-5-(2-(pyridin-2-yl)-1H-imidazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the method described in Example 1, except that 2-(1-benzyl-1H-imidazol-2-yl)pyridine (prepared according to Example 8, Step A, except that commercially available 2-cyanopyridine was used instead of 3-fluorobenzonitrile) was used instead of 1-benzyl-2-phenyl-1H-imidazole in Step C; Rf 0.43 with 95:5 v/v dichloromethane-methanol; melting point 262° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.33 (s, 2H), 8.63 (d, 1H), 8.43-8.37 (m, 2H), 8.16 (d, 1H), 8.06 (d, 1H), 7.94 (dt, 1H), 7.54-7.49 (m, 3H), 7.43-7.39 (m, 1H); MS (ESI+) m/z 300.1 (M+1); H-PGDS FPBA IC50: 0.125 μM; H-PGDS inhibitor EIA IC50: 0.053 μM.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-d7820c2a22ae48aabe652a99c0463037
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Linked notes

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