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

HRID 1717425Notes

Reaction equation

HRID 1717425 reaction equation
CS([O:5][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+].[F:35][CH:36]([F:39])[CH2:37]O>C(#N)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:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=3)[C:7]=2[CH2:6][O:5][CH2:37][CH:36]([F:39])[F:35])=[O:24])[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1361872,2-Difluoroethan-1-olHCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

Product 1

HCID 57664914N-cyclopropyl-5-[(2,2-difluoroethoxy)methyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 83%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-[(Cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate (204 mg, 0.5 mmol) obtained in Example 126a), potassium carbonate (69 mg, 0.5 mmol, 1.0 eq.) and 2,2-difluoroethanol (0.5 ml) were suspended in acetonitrile (3 ml), and the suspension was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (30 ml), washed with saturated aqueous sodium hydrogen carbonate solution and 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, 83%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and 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-937d36a704c14f1e8142734840fd55a8
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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