Cyclohexanone → Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

HRID 2184299Notes

Reaction equation

HRID 2184299 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([NH2:12])=[N:7][CH:6]=1)[CH3:2].[C:14]1(=O)[CH2:19]CC[CH2:16][CH2:15]1>>[NH2:11][C:9]1[C:8]2[N:7]([C:14]([CH3:19])=[C:15]([CH3:16])[N:12]=2)[CH:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:10]=1

Participants

3

Reactant 2

HCID 7967CyclohexanoneHCID 9877541Ethyl 5,6-diaminonicotinate

Product 1

HCID 9942738Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Conditions

Temperature
100 °C

Procedure

To a suspension of 5,6-diamino-nicotinic acid ethyl ester (1 eq., 5.0 g) in cyclohexanone (50 ml) bromobutanone (1.4 equiv., 5.95 g) was added over 15 min. The dark brown mixture was heated to 100° C. (inner temperature) and stirred 1.5 h at this temperature. The mixture was cooled to room temperature and the light brown solid was filtered off and was washed with TBME (20 ml). Drying under reduced pressure at 45° C. Yield: 5.06 g (65%).

Workup

  1. additionwas added over 15 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe light brown solid was filtered off
  4. washwas washed with TBME (20 ml)
  5. customDrying under reduced pressure at 45° C

Sources & evidence

ORD record
ord-8ad388311dcc40bf9016f02e0007224d
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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