Pyridine → HCID 59496133, compound

HRID 1971629Notes

Reaction equation

HRID 1971629 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-b8d9cdb6c1d448d1b8f7081e066c4f31
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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