Pyridine → N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-3,3-dimethyl-butyramide

HRID 1473946Notes

Reaction equation

HRID 1473946 reaction equation
[C:1]([CH2:5][C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:9]1([C:12]2[N:16]3[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]3=[N:14][C:13]=2[NH2:22])[CH2:11][CH2:10]1.N1C=CC=CC=1>C(#N)C>[CH:9]1([C:12]2[N:16]3[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]3=[N:14][C:13]=2[NH:22][C:6](=[O:7])[CH2:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 815143,3-Dimethylbutanoyl chlorideHCID 576074593-Cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-ylamine2×

Product 1

HCID 57607469N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-3,3-dimethyl-butyramide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl acetyl chloride (0.040 mL, 0.00029 mol) was added to a solution of 3-Cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-ylamine (compound f, 0.054 g, 0.00027 mol) in acetonitrile (5.00 mL) containing pyridine (0.0637 g, 0.00081 mol) and the mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and crude product purified by column chromatography (50% ethyl acetate/hexanes to neat ethyl acetate) to give N-(3-cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-3,3-dimethyl-butyramide as a yellow solid. Rf 0.41, 5% methanol/dichloromethane; MS m/z 289 (M+H). SH-SY5Y_EC50 (μM): 2.5464.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and crude product
  2. custompurified by column chromatography (50% ethyl acetate/hexanes to neat ethyl acetate)

Sources & evidence

ORD record
ord-83ec8604ef5b48d2bf0610835a11e51a
Source dataset
uspto-grants-2015_04
Patent number
US09018208B2

Reaction notes

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