Triethylamine hydrochloride → HCID 178440939, compound

HRID 1667650Notes

Reaction equation

HRID 1667650 reaction equation
[C:1]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[CH2:28][CH2:29][C:30]#[N:31])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N-:34]=[N+:35]=[N-:36].[Na+].Cl.C(N(CC)CC)C.CN1CCCC1=O>O>[C:1]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[CH2:28][CH2:29][C:30]2[NH:36][N:35]=[N:34][N:31]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 13387N-methyl-2-pyrrolidoneHCID 33557Sodium AzideHCID 58008024HCID 58008024, compound

Product 1

HCID 178440939HCID 178440939, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-{4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl-3-yl}propionitrile (227 mg, 0.5 mmol), sodium azide (98 mg, 1.5 mmol), triethylamine hydrochloride (103 mg, 0.75 mol) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 150° C. for 4 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (45 mg, 18%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2e61816efddf4166bd2f1881fa1235ca
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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