Hydrochloric Acid → HCID 68516097, compound

HRID 1717352Notes

Reaction equation

HRID 1717352 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]=[N:15][N:16]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:31])=[CH:26][CH:25]=2)[C:17]=1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][F:23])=[O:12])=[O:6].CC(C)([O-])C.[K+].Cl>C1COCC1>[F:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]1[N:16]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:31])=[CH:26][CH:25]=2)[N:15]=[N:14][C:13]=1[C:11]([NH:10][CH2:9][CH2:8][N:7]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 68514586HCID 68514586, compound

Product 1

HCID 68516097HCID 68516097, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-({[(2-chloroethyl)amino]carbonyl}amino)ethyl]-5-(5-fluoropentyl)-1-(4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxamide (0.06 g) obtained in Example 301 in THF (5.5 ml) was added potassium tert-butoxide (0.03 g), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N hydrochloric acid, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC (acetonitrile-water) and recrystallized from acetonitrile-water to give the title compound as a white powder (0.01 g, 14%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by preparative HPLC (acetonitrile-water)
  7. customrecrystallized from acetonitrile-water

Sources & evidence

ORD record
ord-4b8d3e6ac800457a9bf98baff954b78d
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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