Triethylamine → HCID 178522056, compound

HRID 45814

Reaction equation

HRID 45814 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28]([NH:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=4)=[O:29])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178507541HCID 178507541, compound

Product 1

HCID 178522056HCID 178522056, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To 3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (700 mg, 3 mmol) in anhydrous pyridine (15 mL) at 0° C. 4-trifluoromethylphenylisocyanate (420 μL, 3 mmol) was added. The reaction was stirred for 2 hours at 0° C. under nitrogen atmosphere to give a mixture of monourea and bis-urea as regioisomeric mixture. Solvent was removed under reduced pressure. The residue was dissolved in methanol (15 mL) and triethylamine (1 mL, 7.8 mmol) was added and the reaction was stirred at room temperature overnight. After this time only the monourea could be detected by HPLC/MS. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed successively with water (3×50 mL). The crude was purified by silica gel column chromatography (DCM/methanol 9:1) to give the desired product as a white solid (75%).

Workup

  1. customat 0° C
  2. customto give
  3. customSolvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (15 mL)
  5. stirringthe reaction was stirred at room temperature overnight
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  8. washwashed successively with water (3×50 mL)
  9. customThe crude was purified by silica gel column chromatography (DCM/methanol 9:1)

Sources & evidence

ORD record
ord-568357e338334b369eb32b7a7405ce38
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

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