1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 16222146, compound

HRID 1717392Notes

Reaction equation

HRID 1717392 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[O:17])=[CH:12][CH:11]=2)[N:8]=[N:7][C:6]=1[C:24]([NH:26][CH:27]1[CH2:29][CH2:28]1)=[O:25].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[CH:27]1([NH:26][C:24]([C:6]2[N:7]=[N:8][N:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][C:20]([F:21])([F:22])[F:23])=[O:17])=[CH:12][CH:11]=3)[C:5]=2/[CH:4]=[CH:3]/[CH3:2])=[O:25])[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68514522HCID 68514522, compound

Product 1

HCID 16222146HCID 16222146, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

5-(3-Bromopropyl)-N-cyclopropyl-1-(4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxamide (212 mg, 0.45 mmol) obtained in Example 399a) was dissolved in acetonitrile (5.0 ml), tetrabutylammonium fluoride monohydrate (140 mg, 0.54 mmol) was added, and the mixture was stirred at 80° C. for 16 hr. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/9 to 7/3) and recrystallized from ethyl acetate-hexane to give the title compound as a colorless powder (27.7 mg, 16%).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/9 to 7/3)
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f3d877944089492ebc35e1a1f5528a93
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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