Benzimidazole → HCID 178526814, compound

HRID 1363204Notes

Reaction equation

HRID 1363204 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=1.[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:19]1([C:2]2[N:7]=[C:6]([NH:8][C@H:9]3[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]3)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[CH:20]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 178526810HCID 178526810, compound

Product 1

HCID 178526814HCID 178526814, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of trans-4-(2-chloro-5nitropyrimidin-4-ylamino)cyclohexanol (310 mg), benzimidazole (390 mg), and potassium carbonate (0.5 g) was heated in acetonitrile at 60° C. for 2 hours. The mixture was concentrated onto silicon gel and purified by column chromatography (DCM:EtOAc:MeOH 70:22:8) to give 350 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated onto silicon gel
  2. custompurified by column chromatography (DCM:EtOAc:MeOH 70:22:8)

Sources & evidence

ORD record
ord-8bbeb4305b794551b3579cdf803d734a
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…