Diisopropylethylamine → HCID 11646459, compound

HRID 1497480Notes

Reaction equation

HRID 1497480 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.C(N(C(C)C)CC)(C)C.[Cl:22][C:23]1[C:24]([C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=O)=[CH:31][CH:30]=2)=[N:25][CH:26]=[CH:27][CH:28]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:22][C:23]1[C:24]([C:29]2[CH:37]=[CH:36][C:32]([C:33]3[NH:10][C:5]4[CH:4]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:8]=[CH:7][C:6]=4[N:9]=3)=[CH:31][CH:30]=2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11646459HCID 11646459, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.44 g (2.5 mmol) 4-trifluoromethylbenzene-1,2-diamine, 1.0 mL (5.0 mmol) diisopropylethylamine and 1.1 g (6 mmol) O-(7-azabenzotriazol-yl)-N,N,N′,N′-tetramethyleuronium hexafluorophosphate were added to a solution of 0.59 g (2.5 mmol) 4-(3-chloropyridin-2-yl)benzoic acid in 25 mL dimethylformamide, which was then stirred at room temperature for 16 hours and vacuum concentrated. The concentrate thus obtained was dissolved in ethyl acetate, washed with saturated NaHCO3 and saturated NaCl, dried over magnesium sulfate, and concentrated in a vacuum. The residue was dissolved in acetic acid/toluene (15 mL/1.5 mL) and stirred at 75° C. for 3 hours, followed by vacuum concentration. Again, the concentrate was dissolved in ethyl acetate, washed with saturated NaHCO3 and saturated NaCl, dried over magnesium sulfate, and vacuum concentrated. The residue was separated using column chromatography (developing solvent: chloroform/methanol=30/1) to produce 0.77 g of 2-[4-(3-chloropyridin-2-yl)phenyl]-6-trifluoromethyl-1H-benzoimidazole (yield 82%).

Workup

  1. concentrationvacuum concentrated
  2. concentrationThe concentrate thus
  3. customobtained
  4. washwashed with saturated NaHCO3 and saturated NaCl
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. dissolutionThe residue was dissolved in acetic acid/toluene (15 mL/1.5 mL)
  8. stirringstirred at 75° C. for 3 hours
  9. concentrationfollowed by vacuum concentration
  10. dissolutionAgain, the concentrate was dissolved in ethyl acetate
  11. washwashed with saturated NaHCO3 and saturated NaCl
  12. dry with materialdried over magnesium sulfate, and vacuum
  13. concentrationconcentrated
  14. customThe residue was separated

Sources & evidence

ORD record
ord-42368a40c55c49528af423afd4690edc
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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