Triethylamine → HCID 23117187, compound

HRID 900689Notes

Reaction equation

HRID 900689 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].C(N(CC)CC)C.C(O[CH2:18][C:19]1[S:23][C:22]([NH:24][C:25]([C:27]2[CH:28]=[C:29]([Cl:44])[C:30]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:35][CH2:34]3)=[N:31][CH:32]=2)=[O:26])=[N:21][C:20]=1[C:45]1[S:46][CH:47]=[C:48]([Cl:50])[CH:49]=1)(=O)C>CN(C)C1C=CN=CC=1.CCO>[Cl:44][C:29]1[C:30]([N:33]2[CH2:34][CH2:35][CH:36]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:37][CH2:38]2)=[N:31][CH:32]=[C:27]([C:25](=[O:26])[NH:24][C:22]2[S:23][C:19]([CH2:18][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])=[C:20]([C:45]3[S:46][CH:47]=[C:48]([Cl:50])[CH:49]=3)[N:21]=2)[CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 11227037HCID 11227037, compound

Product 1

HCID 23117187HCID 23117187, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

39 μl of N-(2-methoxyethyl)methylamine, 51 μl of triethylamine and 23 mg of 4-(dimethylamino)pyridine were added to a 6 ml EtOH suspension of 107 mg of ethyl 1-(5-{[5-[(acetoxy)methyl]-4-(4-chlorothiophen-2-yl)thiazol-2-yl]carbamoyl}-3-chloro-2-pyridyl)piperidine-4-carboxylate, and the mixture was stirred at 50° C. for 2 hours. After the solvent was distilled off, a saturated sodium hydrogencarbonate aqueous solution was added, and the mixture was extracted with EtOAc, and washed with water and with brine(saturated sodium chloride aqueous solution). The resulting product was dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using a hexane:EtOAc (10:1 to 3.5:1) as an elution solvent to obtain 90 mg of ethyl 1-{3-chloro-5-[(4-(4-chlorothiophen-2-yl)-5-{[(2-methoxyethyl)(methyl)amino]methyl}thiazol-2-yl)carbamoyl]-2-pyridyl}piperidine-4-carboxylate.

Workup

  1. distillationAfter the solvent was distilled off
  2. additiona saturated sodium hydrogencarbonate aqueous solution was added
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with water and with brine(saturated sodium chloride aqueous solution)
  5. dry with materialThe resulting product was dried over magnesium sulfate
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e6ae2baca9554559856363b1edd3635b
Source dataset
uspto-grants-2008_04
Patent number
US07361658B2

Reaction notes

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