Sodium Iodide → 5-[(benzylamino)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717322Notes

Reaction equation

HRID 1717322 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+].[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[I-].[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:35]([NH:42][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])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

Product 1

HCID 576651565-[(benzylamino)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 90%

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 (225 mg, 0.552 mmol) obtained in Example 126a), potassium carbonate (76.3 mg, 0.552 mmol, 1.0 eq.) and benzylamine (0.123 ml, 1.10 mmol, 2.0 eq.) were suspended in acetonitrile (7.5 ml), sodium iodide (16.6 mg, 0.110 mmol, 0.2 eq.) was added, and the mixture 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 (208 mg, 0.497 mmol, 90.0%).

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-d3317ac2b52b43acb22e2f839b8b444c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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