HCID 58577496, compound → HCID 58577636, compound

HRID 1044183Notes

Reaction equation

HRID 1044183 reaction equation
Cl[C:2]1[N:6]([CH2:7][CH:8](OCC)OCC)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:29]3[N:28]([CH2:35][CH3:36])[C:27]2=[O:37])=[CH:22][CH:21]=1>>[CH2:35]([N:28]1[C:29]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[N:26]([C:23]2[CH:22]=[CH:21][C:20]([N:19]3[C:2]4=[N:3][C:4]5[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=5[N:6]4[CH:7]=[CH:8]3)=[CH:25][CH:24]=2)[C:27]1=[O:37])[CH3:36]

Participants

3

Reactant 2

HCID 58577496HCID 58577496, compoundHCID 58577706HCID 58577706, compound

Product 1

HCID 58577636HCID 58577636, compoundYield 31.5%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-1-(2,2-diethoxyethyl)-1H-benzimidazole (860 mg) and 3-(4-aminophenyl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (636 mg) was heated at 150° C. for 50 min. The reaction mixture was partitioned between AcOEt/THF (1/1) and 1 M NaOH aqueous solution. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography eluting with THF and recrystallized from THF to give 1-ethyl-3-[4-(1H-imidazo[1,2-a]benzimidazol-1-yl)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (311 mg).

Workup

  1. customThe reaction mixture was partitioned between AcOEt/THF (1/1) and 1 M NaOH aqueous solution
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography
  7. washeluting with THF
  8. customrecrystallized from THF

Sources & evidence

ORD record
ord-c3315b3ff63249a5a6e978423800390e
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

Loading…