Bromoacetone → HCID 59145920, compound

HRID 887816Notes

Reaction equation

HRID 887816 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[CH:8]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:9][CH2:10][C:5]2=[CH:4][CH:3]=1.Br[CH2:18][C:19](=O)[CH3:20].C(=O)([O-])O.[Na+]>C(O)C>[CH3:20][C:19]1[N:1]=[C:2]2[CH:3]=[CH:4][C:5]3[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[C:6]=3[N:7]2[CH:18]=1

Participants

5

Reactant 3

HCID 11715BromoacetoneHCID 516892Sodium BicarbonateHCID 59145886HCID 59145886, compound

Product 1

HCID 59145920HCID 59145920, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of N-[2-(2-amino-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)ethyl]acetamide (17.6 mg, 0.0803 mmol), bromoacetone (16.5 mg, 0.120 mmol) and sodium hydrogen carbonate (10.1 mg, 0.12 mmol) in ethanol (1 mL) was heated under reflux for 4 hr. The solvent was evaporated under reduced pressure, and N,N-dimethylformamide (1 mL) was added. The mixture was irradiated with 150 W microwave and stirred at 160° C. for 30 min. The solvent was evaporated under reduced pressure, and the residue was purified by thin layer chromatography (methanol/ethyl acetate=17/83 and NH; methanol/ethyl acetate=5/95) to give the title compound (2.0 mg, yield 10%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. customThe solvent was evaporated under reduced pressure, and N,N-dimethylformamide (1 mL)
  4. additionwas added
  5. customThe mixture was irradiated with 150 W microwave
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by thin layer chromatography (methanol/ethyl acetate=17/83 and NH; methanol/ethyl acetate=5/95)

Sources & evidence

ORD record
ord-8ad35d9d85a04054a3140de719c42645
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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