Diisopropylethylamine → HCID 178448869, compound

HRID 2276766Notes

Reaction equation

HRID 2276766 reaction equation
Br[C:2]1[N+:3]([O-:8])=[N:4][CH:5]=[CH:6][N:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C>CC#N>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH:18][C:2]2[N+:3]([O-:8])=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3213073-Bromo-2-oxo-1,2lambda~5~,4-triazineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Product 1

HCID 178448869HCID 178448869, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-bromo-1,2,4-triazin-2-oxide (2.0 g, 11 mmol), (2-(4-fluorophenyl)-2-methylpropan-1-amine (3.0 g, 17 mmol), and diisopropylethylamine (3.0 mL, 17 mmol) in CH3CN (20 mL) was stirred at rt for 24 h. The solvents were removed and the residue dissolved in EtOAc. The solution was washed with saturated NaHCO3, dried over Na2SO4, and evaporated to dryness. The residue was mixed with ether and then filtered to give the desired product (1.2 g) as a yellow solid.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe solution was washed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. additionThe residue was mixed with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4c2360b15dac4ab6aba499c58811fb16
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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