Ethyl Acetate → Ethyl 1-{5-[({[8-(cyclohexylmethoxy)-2-methylimidazolo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-3-carboxylate

HRID 64486

Reaction equation

HRID 64486 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[C:15]3=[N:14][C:13]=2[CH3:29])=[O:11])=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:31]1.[Cl-].[NH4+].C(OCC)(=O)C>CN1CCCC1=O>[CH:23]1([CH2:22][O:21][C:20]2[C:15]3[N:16]([C:12]([C:10]([NH:9][CH2:8][C:5]4[CH:4]=[CH:3][C:2]([N:30]5[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:31]5)=[N:7][CH:6]=4)=[O:11])=[C:13]([CH3:29])[N:14]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 98969Ethyl nipecotateHCID 86713518N-[(6-chloropyridin-3-yl)methyl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86713519Ethyl 1-{5-[({[8-(cyclohexylmethoxy)-2-methylimidazolo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 70 mg of N-[(6-chloropyridin-3-yl)methyl]-8-(cyclohexylmethoxy)-2-methylimidazolo[1,2-a]pyridine-3-carboxamide in 1 mL of N-methyl-2-pyrrolidone was added 0.12 mL of ethyl piperidine-3-carboxylate to carry out a reaction at 240° C. for 50 minutes under microwave irradiation. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 43 mg of ethyl 1-{5-[({[8-(cyclohexylmethoxy)-2-methylimidazolo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-3-carboxylate.

Workup

  1. customa reaction at 240° C. for 50 minutes
  2. customunder microwave irradiation
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea84972a54ae4ade9e1c17560f042844
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Linked notes

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