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

HRID 2184300Notes

Reaction equation

HRID 2184300 reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[N:8][CH:7]=1)([CH3:3])[CH3:2].[C:15]1(=O)[CH2:20]CC[CH2:17][CH2:16]1>>[NH2:12][C:10]1[C:9]2[N:8]([C:15]([CH3:20])=[C:16]([CH3:17])[N:13]=2)[CH:7]=[C:6]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:14])[CH:11]=1

Participants

3

Reactant 2

HCID 7967CyclohexanoneHCID 9855728Isopropyl 5,6-diaminonicotinate

Product 1

HCID 9942912Isopropyl 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 isopropyl ester (1 eq., 5.1 g) in cyclohexanone (50 ml) bromobutanone (1.2 equiv., 3.4 ml) was added over 10 min. The dark brown mixture was heated to 100° C. (inner temperature) and stirred 1.5 h at this temperature. The suspension was cooled to room temperature and the pale yellow solid was filtered off and was washed with TBME (3×10 ml). Drying under reduced pressure at 45° C. Yield: 6.0 g (74%).

Workup

  1. additionwas added over 10 min
  2. temperatureThe suspension was cooled to room temperature
  3. filtrationthe pale yellow solid was filtered off
  4. washwas washed with TBME (3×10 ml)
  5. customDrying under reduced pressure at 45° C

Sources & evidence

ORD record
ord-7a8758ab59804e71ba108516bf296f41
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

Loading…