Triethylamine → 1-[2-(4-Ethyl-piperazin-1-yl)-pyridin-4-yl]-3-propyl-urea

HRID 272533Notes

Reaction equation

HRID 272533 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[N:23]([CH2:26][CH2:27][CH3:28])=[C:24]=[O:25]>ClCCl>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[C:13]([NH:15][C:24]([NH:23][CH2:26][CH2:27][CH3:28])=[O:25])[CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 617095722-(4-Ethylpiperazin-1-yl)pyridin-4-amine

Product 1

HCID 116664581-[2-(4-Ethyl-piperazin-1-yl)-pyridin-4-yl]-3-propyl-ureaYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 20.6 mg (0.1 mmol) 2-(4-ethyl-piperazin-1-yl)-pyridin-4-ylamine, 15 mg (0.15 mmol) triethylamine and 9.4 mg (0.11 mmol) 1-isocyanato-propane in 1 ml dichloromethane 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 7.2 mg (25%) 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-cb403ed8becd4606b4da5103897c3c91
Source dataset
uspto-grants-2008_11
Patent number
US07456175B2

Reaction notes

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