Triethylamine → 1-[6-(4-Ethyl-piperazin-1-yl)-pyridin-3-yl]-3-propyl-urea

HRID 490082Notes

Reaction equation

HRID 490082 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH:2](C)C.C(N(CC)CC)C.[N:25]([CH2:28][CH2:29][CH3:30])=[C:26]=[O:27]>C(Cl)Cl>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][C:14]([NH:17][C:26]([NH:25][CH2:28][CH2:29][CH3:30])=[O:27])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 242534636-(4-Isobutylpiperazin-1-yl)pyridin-3-amine

Product 1

HCID 117020221-[6-(4-Ethyl-piperazin-1-yl)-pyridin-3-yl]-3-propyl-ureaYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 20 mg (0.1 mmol) 6-(4-isobutyl-piperazin-1-yl)-pyridin-3-ylamine, 15 mg (0.15 mmol) triethylamine and 9.4 mg (0.11 mmol) 1-isocyanato-propane in 1 ml DCM was stirred at room temperature for 16 h. After evaporation the residue was taken up in 1 ml methanol/acetonitrile 1/1 and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 15.5 mg (53%) of the title compound. (m/e): 292.3 (MH+; 100%).

Workup

  1. customAfter evaporation the residue
  2. customsubjected to preparative HPLC purification on reversed phase
  3. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  4. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-13a7411cb12f4d7489dbda0fb47c47a7
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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