4-(Morpholin-4-yl)benzene-1,2-diamine → HCID 25063039, compound

HRID 2089120Notes

Reaction equation

HRID 2089120 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([NH2:31])[C:27]([NH2:30])=[CH:28][CH:29]=2)[CH2:20][CH2:19]1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[N:4][C:3]=1[C:10]1[CH:17]=[CH:16][C:13]([C:14]2[NH:31][C:26]3[CH:25]=[C:24]([N:21]4[CH2:22][CH2:23][O:18][CH2:19][CH2:20]4)[CH:29]=[CH:28][C:27]=3[N:30]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamineHCID 57825691HCID 57825691, compound

Product 1

HCID 25063039HCID 25063039, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

0.50 g of 4-(3-chloro-5-(hydroxymethyl)pyridin-2-yl)benzaldehyde (3) (2.02 mmol) prepared in Example 1 and 0.39 g of 4-morpholinobenzene-1,2-diamine (18) (2.02 mmol) prepared in Example 12 were dissolved in nitrobenzene (5.5 mL), and refluxed under heating for 2 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1) to obtain 0.68 g of {5-chloro-6-[4-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-phenyl]-pyridin-3-yl}-methanol (yield 80%).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9e650baca4c64346a866b47e1f876f1d
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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