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

HRID 1717326Notes

Reaction equation

HRID 1717326 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+].[S-:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Na+]>C(O)C.C(OCC)(=O)C.CCCCCC>[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:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:24])[CH2:28][CH2:27]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 4110039Sodium benzenethiolateHCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

Product 1

HCID 57664805N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylthio)methyl]-1H-1,2,3-triazole-4-carboxamideYield 90.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-[(Cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate (310 mg, 0.761 mmol) obtained in Example 126a), potassium carbonate (52.6 mg, 0.380 mmol, 0.5 eq.) and sodium thiophenoxide (168 mg, 1.14 mmol, 1.5 eq.) were dissolved in ethanol (6.0 ml), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (30 ml) and hexane (2 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 (290 mg, 0.688 mmol, 90.4%).

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-049c13bfee1e46f782b96084ffe4ff2c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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