Water → HCID 67270144, compound

HRID 1695556Notes

Reaction equation

HRID 1695556 reaction equation
Cl.[C:2]1([C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=3)=[O:14])[N:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:35]1([C:41](Cl)=[O:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.O>C1COCC1>[N:35]1([C:41]([N:25]2[CH2:24][CH:23]=[C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:13]([C:11]3[N:12]=[C:8]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[S:9][CH:10]=3)=[O:14])[CH2:27][CH2:26]2)=[O:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 67269961HCID 67269961, compound

Product 1

HCID 67270144HCID 67270144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 170 mg of 2-phenyl-N-[2-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-1,3-thiazole-4-carboxamide hydrochloride in 7 ml of THF was added 0.30 ml of triethylamine, and 60 μl of 4-morpholinecarbonylchloride was added thereto under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction liquid was added 100 ml of water, followed by extraction with EtOAc, and the organic layer was washed with saturated brine, dried over sodium sulfate, and then filtered. A solvent was evaporated under reduced pressure, and the residue was recrystallized from 5 ml of ethanol to obtain 165 mg of N-{2-[1-(4-morpholinylcarbonyl)-1,2,3,6-tetrahydro-4-pyridinyl]phenyl}-2-phenyl-1,3-thiazole-4-carboxamide.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with EtOAc
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customA solvent was evaporated under reduced pressure
  9. customthe residue was recrystallized from 5 ml of ethanol

Sources & evidence

ORD record
ord-cf4c8b76eb984c9c994ec4a2a12c55e9
Source dataset
uspto-grants-2012_04
Patent number
US08163746B2

Reaction notes

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