Potassium Carbonate → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(methylthio)methyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717325Notes

Reaction equation

HRID 1717325 reaction equation
CS(O[CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)[N:10]=[N:9][C:8]=1[C:23]([NH:25][CH:26]1[CH2:28][CH2:27]1)=[O:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:35][S-:36].[Na+]>C(O)C.C(OCC)(=O)C>[CH:26]1([NH:25][C:23]([C:8]2[N:9]=[N:10][N:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:17]=3)[C:7]=2[CH2:6][S:36][CH3:35])=[O:24])[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolateHCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

Product 1

HCID 57664803N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(methylthio)methyl]-1H-1,2,3-triazole-4-carboxamideYield 92.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-[(Cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate (196 mg, 0.481 mmol) obtained in Example 126a), potassium carbonate (33.2 mg, 0.241 mmol, 0.5 eq.) and 15% aqueous sodium thiomethoxide solution (0.449 ml, 0.962 mmol, 2.0 eq.) were dissolved in ethanol (3.5 ml), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (30 ml), washed twice with 2% aqueous sodium carbonate solution and with saturated brine, dried over anhydrous sodium sulfate and concentrated. Diethyl ether was added and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (160 mg, 0.445 mmol, 92.5%).

Workup

  1. washwashed twice with 2% aqueous sodium carbonate solution and with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. additionDiethyl ether was added
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-29567c83a13f4422a88ac163317e44be
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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