Morpholine → Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-morpholinobenzimidazole-7-carboxylate

HRID 494339Notes

Reaction equation

HRID 494339 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])=[CH:10][CH:9]=2)[C:5]2[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=2[N:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:5]3[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=3[N:3]=[C:2]2[N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:9][CH:10]=1)#[N:21]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 15654692Methyl 2-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate

Product 1

HCID 15654693Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-morpholinobenzimidazole-7-carboxylateYield 77%

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-chloro-1-[(2′-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate (0.8 g) in morpholine (15 ml) was stirred at 100° C. for 2 hours and the reaction mixture was concentrated to dryness. The residue was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The resulting crystals were recrystallized from ethyl acetate-hexane to afford colorless prisms (0.69 g, 77%).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2a224978509342a3bce5378d068db50e
Source dataset
uspto-grants-2009_05
Patent number
US07538133B2

Reaction notes

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