Acetonitrile → ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate

HRID 64464Notes

Reaction equation

HRID 64464 reaction equation
Cl.Cl.[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][C@H:24]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.[C:39]([O:42][CH2:43][CH2:44]Br)(=[O:41])[CH3:40]>C(Cl)(Cl)Cl.O.CN(C=O)C>[CH2:43]([O:42][C:39](=[O:41])[CH2:40][N:26]1[CH2:27][CH2:28][CH2:29][C@H:24]([NH:23][C:21]([C:17]2[N:13]3[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[C:12]3=[N:19][C:18]=2[CH3:20])=[O:22])[CH2:25]1)[CH3:44]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 867134908-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Product 1

HCID 131737222ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 307 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride, 335 mg of potassium carbonate, 5 ml of acetonitrile, and 5 ml of DMF was added 92 μl of bromoethyl acetate under ice-cooling, followed by stirring for 3 hours under ice-cooling. To the reaction mixture were added water and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 299 mg of ethyl[(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)piperidin-1-yl]acetate.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customa layer separation operation
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e976c4e9c9f48098fa2f6a15b511287
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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