Piperidine → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-piperidin-1-ylpyridine-3,5-dicarbonitrile

HRID 1913499Notes

Reaction equation

HRID 1913499 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](SC)[C:5]([C:12]#[N:13])=[C:4]([S:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[S:19][CH:20]=2)[N:3]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[Cl-].[NH4+].C(OCC)(=O)C>CC(C)=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:5]([C:12]#[N:13])=[C:4]([S:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[S:19][CH:20]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 666721182-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methylthio)pyridine-3,5-dicarbonitrile

Product 1

HCID 249684742-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-piperidin-1-ylpyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.00 g (11.63 mmol) of the compound from Example 44A and 57.50 ml (581.43 mmol) of piperidine were initially charged in 120 ml of acetone and heated at reflux for 8 h. After cooling, the mixture was poured into a solvent mixture of 50 ml of saturated aqueous ammonium chloride solution and 50 ml of ethyl acetate. The phases were separated. The organic phase was washed twice with in each case 20 ml of saturated aqueous sodium chloride solution and then dried over magnesium sulfate. After removal of the solvent, the residue was triturated with 100 ml of diethyl ether. The precipitate was filtered off with suction and dried under reduced pressure at 50° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 h
  3. temperatureAfter cooling
  4. customThe phases were separated
  5. washThe organic phase was washed twice with in each case 20 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was triturated with 100 ml of diethyl ether
  9. filtrationThe precipitate was filtered off with suction
  10. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-f8a8f8b1f8764d1c861ed6a6457d6352
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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