Hydrochloric Acid → 1-[4-({[2-(4-methylpiperazin-1-yl)ethyl]amino}carbonyl)phenyl]-5-propyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717277Notes

Reaction equation

HRID 1717277 reaction equation
[N:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:23]([CH2:30][CH2:31][CH3:32])[CH2:24][C:25]([O:27]CC)=[O:26].[O-]CC.[Na+].Cl>C(O)C>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][NH:10][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N:1]3[C:23]([CH2:30][CH2:31][CH3:32])=[C:24]([C:25]([OH:27])=[O:26])[N:3]=[N:2]3)=[CH:21][CH:20]=2)=[O:9])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 866298014-azido-N-[2-(4-methylpiperazin-1-yl)ethyl]benzamide

Product 1

HCID 685151961-[4-({[2-(4-methylpiperazin-1-yl)ethyl]amino}carbonyl)phenyl]-5-propyl-1H-1,2,3-triazole-4-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Azido-N-[2-(4-methylpiperazin-1-yl)ethyl]benzamide obtained in Example 63b) and ethyl 3-oxohexanoate (0.503 ml, 2.99 mmol, 1.25 eq.) were dissolved in ethanol (15 ml), sodium ethoxide (226 mg, 2.99 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 60° C. for 10.5 hr. 1N hydrochloric acid (3.0 ml) was added to the reaction mixture, and the mixture was concentrated. The residue was diluted with acetonitrile (20 ml) and ethanol (40 ml), and the mixture was concentrated. Ethanol (15 ml), THF (20 ml) and ethyl acetate (20 ml) were added to the residue. The precipitate was collected by filtration, washed with ethyl acetate and dried to give the title compound as a pale-brown powder (purity 90%, containing sodium chloride, 1.04 g, 2.33 mmol, 98.2%).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with acetonitrile (20 ml) and ethanol (40 ml)
  3. concentrationthe mixture was concentrated
  4. additionEthanol (15 ml), THF (20 ml) and ethyl acetate (20 ml) were added to the residue
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-dcdae3f03521438f92f668f382bb473a
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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