Triethylamine → HCID 67389250, compound

HRID 1929402Notes

Reaction equation

HRID 1929402 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C@@H:11]1[C@@H:16]([NH2:17])[CH2:15][C@@H:14]2[CH2:18][C@H:12]1[C:13]2([CH3:20])[CH3:19].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[CH3:10][C@@H:11]1[C@@H:16]([NH:17][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:15][C@@H:14]2[CH2:18][C@H:12]1[C:13]2([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678552-FluorobenzonitrileHCID 44515885HCID 44515885, compound

Product 1

HCID 67389250HCID 67389250, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2-Fluorobenzonitrile (100 mg), (1R,2S,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine (380 mg), triethylamine (1.5 mL) were dissolved in anhydrous dimethylsulfoxide (5 mL) and heated at 130° C. overnight. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column purification with 0-5% methanol/dichloromethane to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column purification with 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-75bbc7cb41ad441fb74cb775ce160d5a
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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