Pyridine → HCID 59496133, compound

HRID 556326Notes

Reaction equation

HRID 556326 reaction equation
[CH3:1][C:2]1[N:7]2[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:28]([CH2:32][C:33](Cl)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[CH3:29][C:28]([CH3:31])([CH3:30])[CH2:32][C:33]([NH:11][C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]2[C:8]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=1)=[O:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 815143,3-Dimethylbutanoyl chlorideHCID 59496138HCID 59496138, compound2×

Product 1

HCID 59496133HCID 59496133, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Methyl-3-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-2-ylamine (compound s, 0.05 g, 0.0002 mol) was dissolved in acetonitrile (0.9 mL) and pyridine (0.03 mL, 0.0003 mol). t-butylacetyl chloride (0.028 mL, 0.00020 mol) was added and the mixture was stirred at room temperature for 4 hours. Solvent was removed then ethyl acetate and saturated sodium bicarbonate was added. The layers were separated and the organic layer dried (magnesium sulfate) then removed. The crude product was chromatographed using 60% ethyl acetate/hexanes to give 39 mg of 3,3-Dimethyl-N-[5-methyl-3-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-2-yl]-butyramide as a white solid. Rf 0.27, 100% ethyl acetate; MS m/z 390 (M+H). SH-SY5Y_EC50: 0.3399.

Workup

  1. customSolvent was removed
  2. additionethyl acetate and saturated sodium bicarbonate was added
  3. customThe layers were separated
  4. dry with materialthe organic layer dried (magnesium sulfate)
  5. customthen removed
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-f8d510be3789439bb1b91d801658e024
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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