2-Butanone, 3-bromo- → 8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

HRID 2184302Notes

Reaction equation

HRID 2184302 reaction equation
[NH2:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].Br[CH:13]([CH3:17])[C:14](=O)[CH3:15]>C1(=O)CCCCC1>[NH2:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:15])[N:11]=2)[CH:5]=[C:6]([C:7]([NH2:9])=[O:8])[CH:10]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 99421905,6-Diaminonicotinamide

Product 1

HCID 98557898-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamideYield 129.5%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Conditions

Temperature
20 °C

Procedure

5,6-Diamino-nicotinamide (30.0 g; 0.183 mol; 1.0 equiv) was suspended in cyclohexanone (280 mL). 3-Bromo-2-butanone (24 mL; 0.22 mol; 1.2 equiv) was added and the mixture was heated for 4 h to 100° C. The reaction mixture was cooled to 20° C. and allowed to stir for another 2 h. The solid was filtered off, washed with TBME (200 mL) and dried to yield 48.4 g of the title compound. Yield: 78%.

Workup

  1. temperaturethe mixture was heated for 4 h to 100° C
  2. filtrationThe solid was filtered off
  3. washwashed with TBME (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-998e42ba58a342908f8a02dadeb96638
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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