Triethylamine → 3-Amino-6-bromo-N'-(3,3,3-trifluoro-2-methyl-2-(triisopropylsilyloxy)propanoyl)-5-(trifluoromethyl)picolinohydrazide

HRID 574209Notes

Reaction equation

HRID 574209 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=[O:25])[C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])(=O)=O>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=[O:25])[C:18]([CH3:23])([O:24][Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[C:19]([F:22])([F:21])[F:20])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 867295963-Amino-6-bromo-N'-(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)-5-(trifluoromethyl)picolinohydrazide

Product 1

HCID 867295973-Amino-6-bromo-N'-(3,3,3-trifluoro-2-methyl-2-(triisopropylsilyloxy)propanoyl)-5-(trifluoromethyl)picolinohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-amino-6-bromo-W-(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)-5-(trifluoromethyl)picolinohydrazide (step 1) (4 g, 9.11 mmol) in DCM (60 ml), triethylamine (1.270 ml, 9.11 mmol) was added to give a yellow solution. The solution was cooled to 0° C. (ice bath) and treated with triisopropylsilyl trifluoromethanesulfonate (4.94 ml, 18.22 mmol). The reaction mixture was stirred at 0° C. for 1 hour and allowed to warm to RT and stirred for 3 days. The reaction mixture was partitioned between DCM (100 ml) and water (100 ml), phases shaken and separated. The organic portion was washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo. The resulting oil was purified by chromatography on silica eluting with 0-30% DCM in iso-hexane to afford the title compound; LC-MS Rt=1.58 min [M+H]+ 595/597 Method 2minLC_v003.

Workup

  1. additionwas added
  2. customto give a yellow solution
  3. temperatureto warm to RT
  4. stirringstirred for 3 days
  5. customThe reaction mixture was partitioned between DCM (100 ml) and water (100 ml), phases
  6. stirringshaken
  7. customseparated
  8. washThe organic portion was washed with brine (100 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe resulting oil was purified by chromatography on silica eluting with 0-30% DCM in iso-hexane

Sources & evidence

ORD record
ord-1a50acdd9e464669b5cc3bc31d9b8b8f
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

Loading…