Triethylamine → HCID 57664845, compound

HRID 1717383Notes

Reaction equation

HRID 1717383 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH:25]4[CH2:27][CH2:26]4)=[O:23])=[CH:18][CH:17]=3)[C:11]=2[CH2:12][CH2:13][CH2:14]O)=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.CS(Cl)(=O)=O.O.[F-:41].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH:25]4[CH2:27][CH2:26]4)=[O:23])=[CH:18][CH:17]=3)[C:11]=2[CH2:12][CH2:13][CH2:14][F:41])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68511447HCID 68511447, compound

Product 1

HCID 57664845HCID 57664845, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-cyclopropyl-1-{4-[(cyclopropylamino)carbonyl]phenyl}-5-(3-hydroxypropyl)-1H-1,2,3-triazole-4-carboxamide (240 mg, 0.65 mmol) obtained in Example 351a) and triethylamine (140 μl, 1.00 mmol) in dichloromethane (10 ml) was added methanesulfonyl chloride (60 μl, 0.78 mmol), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in acetonitrile (10 ml), tetrabutylammonium fluoride monohydrate (425 mg, 1.63 mmol) was added, and the mixture was stirred at 80° C. for 16 hr. After the reaction mixture was allowed to cool to room temperature, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) and recrystallized from ethyl acetate-hexane to give the title compound as a colorless powder (90 mg, 37%).

Workup

  1. washThe reaction mixture was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in acetonitrile (10 ml)
  5. stirringthe mixture was stirred at 80° C. for 16 hr
  6. temperatureto cool to room temperature
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bfd566d7f24c43b5861fb03cb46219da
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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