2-Chlorobenzimidazole → N-(4-(3-methylpyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

HRID 1880049Notes

Reaction equation

[CH3:1][C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CC(O)C>[CH3:1][C:2]1[C:3]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:17]3[NH:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=3)=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 4-(3-methylpyridin-2-yloxy)benzenamine (1.00 g, 4.99 mmol) and 2-chlorobenzimidazole (0.860 g, 5.64 mmol) in 10 mL of iPrOH was heated at 170° C. for 30 min in the microwave. The reaction mixture was evaporated onto silica gel. Purification by flash chromatography (2M NH3 in MeOH:CH2Cl2) afforded N-(4-(3-methylpyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine as solid. MS (ESI, pos. ion) m/z: 317.1 (M+1). IC50 (uM) ++++.

Workup

customThe reaction mixture was evaporated onto silica gel
customPurification by flash chromatography (2M NH3 in MeOH:CH2Cl2)

Sources & evidence

ORD record: ord-a90b5ef7dc264e8e97faf6113d403c19
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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