Potassium Carbonate → 1-{4-[({[8-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-4-carboxylic acid

HRID 64485Notes

Reaction equation

HRID 64485 reaction equation
ClC1N=CC([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])=CC=1.[NH:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38]CC)=[O:37])[CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+].[CH3:49][N:50]1[CH2:54][CH2:53][CH2:52][C:51]1=O>C(OCC)(=O)C>[CH:23]1([CH2:22][O:21][C:20]2[C:15]3[N:16]([C:12]([C:10]([NH:9][CH2:8][C:53]4[CH:54]=[CH:49][N:50]=[C:51]([N:30]5[CH2:31][CH2:32][CH:33]([C:36]([OH:38])=[O:37])[CH2:34][CH2:35]5)[CH:52]=4)=[O:11])=[C:13]([CH3:29])[N:14]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 25517Ammonium ChlorideHCID 70770Ethyl 4-piperidinecarboxylateHCID 86713518N-[(6-chloropyridin-3-yl)methyl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 867135171-{4-[({[8-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 32 mg of N-[(6-chloropyridin-3-yl)methyl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 0.6 ml of N-methyl-2-pyrrolidone was added 0.05 ml of ethyl piperidine-4-carboxylate to carry out a reaction at 150° C. for 30 minutes and further at 200° C. for 30 minutes under microwave irradiation. 24 mg of potassium carbonate was added thereto to carry out a reaction at 240° C. for 2 hours 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 water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography. To the obtained purified product were added hexane and isopropyl ether, and the resulting solid was collected by filtration and dried to obtain 14 mg of 1-{4-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)methyl]pyridin-2-yl}piperidine-4-carboxylic acid.

Workup

  1. customa reaction at 150° C. for 30 minutes
  2. customfurther at 200° C. for 30 minutes under microwave irradiation
  3. customa reaction at 240° C. for 2 hours
  4. customunder microwave irradiation
  5. customa layer separation operation
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography
  10. customTo the obtained purified product
  11. additionwere added hexane and isopropyl ether
  12. filtrationthe resulting solid was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-72d58598dcac4f78ac5fa6e061a0dfdf
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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