Triethylamine → HCID 22272628, compound

HRID 1064856Notes

Reaction equation

HRID 1064856 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)=[C:8]([S:20][CH2:21][CH3:22])[CH:7]=[C:6]([CH3:23])[N:5]=1)[CH3:2].C(N(CC)CC)C.[CH2:31]([NH:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][OH:49])[CH2:43][CH2:42]1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C1(C)C=CC=CC=1.O>[CH2:1]([S:3][C:4]1[C:9]([NH:10][C:11](=[O:19])[N:38]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][OH:49])[CH2:43][CH2:42]2)=[C:8]([S:20][CH2:21][CH3:22])[CH:7]=[C:6]([CH3:23])[N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22272701HCID 22272701, compoundHCID 69731041HCID 69731041, compound

Product 1

HCID 22272628HCID 22272628, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of this phenyl carbamate (1.46 g, 4.19 mmol) in toluene (20 ml) were added triethylamine (509 mg, 5.03 mmol) and 2-[4-(2-heptylaminoethyl)piperazin-1-yl]ethanol (1.14 g, 4.20 mmol) obtained in Example 16 and the mixture was stirred at 80° C. for 2 hours. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 100 g, developing solvent; chloroform:methanol=40:1 20:1) to provide 1.95 g (yield 88%) of N′-[2,4-bis(ethylthio)-6-methyl-3-pyridyl]-N-heptyl-N-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]urea as pale yellow oil.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (silica gel 100 g, developing solvent; chloroform:methanol=40:1 20:1)

Sources & evidence

ORD record
ord-4ec9b1dfb8684073b0838358267fca04
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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