1,1'-Carbonyldiimidazole → 1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

HRID 707276Notes

Reaction equation

HRID 707276 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([NH2:11])=[N:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13]>O1CCOCC1.CCOC(C)=O>[CH:1]1([N:4]2[C:5]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[NH:11][C:12]2=[O:13])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86694145N3-cyclopropylpyridine-2,3-diamine

Product 1

HCID 183348751-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N3-cyclopropylpyridine-2,3-diamine (1.0 g, 6.70 mmol) in dioxane (13.41 ml) was added 1,1′-carbonyldiimidazole (Acros Organics, 1.630 g, 10.05 mmol). The resulting mixture was heated to 60° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was loaded onto a Biotage samplet and purified (0-100% EtOAc/hexane, 25G biotage column) to afford product that solidified upon rotovap. Material was advanced to the next step. M+1: 176.0.

Workup

  1. washwashed with water
  2. custompurified (0-100% EtOAc/hexane, 25G biotage column)
  3. customto afford product that

Sources & evidence

ORD record
ord-881f7c09a854422f9fa882fadd76a358
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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