Ethyl 4-piperidinecarboxylate → HCID 23117199, compound

HRID 900691Notes

Reaction equation

HRID 900691 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[Cl:12][C:13]1[C:14](Cl)=[N:15][CH:16]=[C:17]([CH:39]=1)[C:18]([NH:20][C:21]1[S:22][C:23]([CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[C:24]([C:26]2[S:27][CH:28]=[C:29]([Cl:31])[CH:30]=2)[N:25]=1)=[O:19]>C1COCC1>[Cl:12][C:13]1[C:14]([N:1]2[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]2)=[N:15][CH:16]=[C:17]([C:18](=[O:19])[NH:20][C:21]2[S:22][C:23]([CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[C:24]([C:26]3[S:27][CH:28]=[C:29]([Cl:31])[CH:30]=3)[N:25]=2)[CH:39]=1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 23117206HCID 23117206, compound

Product 1

HCID 23117199HCID 23117199, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.3 ml of ethyl isonipecotate was added to a 5 ml THF solution of 413 mg of 5,6-dichloro-N-[4-(4-chlorothiophen-2-yl)-5-(piperidin-1-ylmethyl)-1,3-thiazol-2-yl]nicotinamide, and the mixture was stirred for 5 days. After the solvent was distilled off under reduced pressure, a saturated sodium hydrogencarbonate aqueous solution was added, and the resulting precipitate was collected by filtration. The precipitate was dissolved in chloroform, and a saturated sodium hydrogencarbonate aqueous solution was added. The mixture was extracted with chloroform, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using hexane:EtOAc (4:1 to 3:1) as an elution solvent to obtain 468 mg of ethyl 1-(3-chloro-5-{[4-(4-chlorothiophen-2-yl)-5-(piperidinomethyl)thiazol-2-yl]carbamoyl}-2-pyridyl)piperidine-4-carboxylate.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additiona saturated sodium hydrogencarbonate aqueous solution was added
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in chloroform
  5. additiona saturated sodium hydrogencarbonate aqueous solution was added
  6. extractionThe mixture was extracted with chloroform
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f38df0b3102f47a196448104e1347c74
Source dataset
uspto-grants-2008_04
Patent number
US07361658B2

Reaction notes

Loading…