Diisopropylethylamine → HCID 11646459, compound

HRID 1497486Notes

Reaction equation

HRID 1497486 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(O)(=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 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

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-1-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 for 5 min, irradiated for 15 min with microwaves in a microwave reactor (Initiator Sixty, Biotage) and concentrated in a vacuum. The concentrate was dissolved in ethyl acetate, washed with saturated NaHCO3 and saturated NaCl, and dried over magnesium sulfate, followed by vacuum concentration. The residue thus obtained was dissolved in acetic acid (15 mL) and stirred for 5 min before irradiation for 15 min with microwaves in a microwave reactor (Initiator Sixty, Biotage). Again, the reaction solution was cooled to room temperature, vacuum concentrated, dissolved in ethyl acetate, washed with saturated NaHCO3 and saturated NaCl, and dried over magnesium sulfate, followed by vacuum concentration. The residue was separated using column chromatography (developing solvent: chloroform/methanol=30/1) to produce 0.81 g of 2-[4-(3-chloropyridin-2-yl)phenyl]-6-trifluoromethyl-1H-benzoimidazole (yield 90%).

Workup

  1. customirradiated for 15 min with microwaves in a microwave reactor (Initiator Sixty, Biotage)
  2. concentrationconcentrated in a vacuum
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and saturated NaCl
  5. dry with materialdried over magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue thus obtained
  8. stirringstirred for 5 min before irradiation for 15 min with microwaves in a microwave reactor (Initiator Sixty, Biotage)
  9. concentrationvacuum concentrated
  10. dissolutiondissolved in ethyl acetate
  11. washwashed with saturated NaHCO3 and saturated NaCl
  12. dry with materialdried over magnesium sulfate
  13. concentrationfollowed by vacuum concentration
  14. customThe residue was separated

Sources & evidence

ORD record
ord-e82dfe6c23e04178a7728d42da34fd19
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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