Triethylamine → Raf265

HRID 15087

Reaction equation

HRID 15087 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=S)=[CH:5][CH:4]=1.[F:14][C:15]([F:38])([F:37])[C:16]1[NH:20][C:19]([C:21]2[CH:26]=[C:25]([O:27][C:28]3[CH:29]=[C:30]([NH2:36])[C:31]([NH:34][CH3:35])=[CH:32][CH:33]=3)[CH:24]=[CH:23][N:22]=2)=[N:18][CH:17]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(#N)C.O>[CH3:35][N:34]1[C:31]2[CH:32]=[CH:33][C:28]([O:27][C:25]3[CH:24]=[CH:23][N:22]=[C:21]([C:19]4[NH:20][C:16]([C:15]([F:37])([F:14])[F:38])=[CH:17][N:18]=4)[CH:26]=3)=[CH:29][C:30]=2[N:36]=[C:10]1[NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1371344-(Trifluoromethyl)phenyl isothiocyanateHCID 1670692-Chloro-1-methylpyridinium iodideHCID 575318901,2-Benzenediamine,n1-methyl-4-[[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]-4-pyridinyl]oxy]-

Product 1

HCID 11656518Raf265Yield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-Trifluoromethylphenyl isothiocyanate (200 mg, 1 mmol) was added to a mixture of 4-(2-(5-(trifluoromethyl)-1H-imidazol-2-yl)pyridin-4-yloxy)-N1-methylbenzene-1,2-diamine (350 mg, 1 mmol) in 3 mL of acetonitrile. After stirring for 20 min at ambient temperature, HPLC analysis showed complete conversion. Triethylamine (0.3 mL, 2.2 mmol) was added followed by 2-chloro-1-methylpyridinium iodide (270 mg, 1.05 mmol). The reaction mixture was heated to 50° C. for 5 h. The heating was stopped and 1.5 mL of water was added. After stirring the mixture for 2 h, the solid was collected by filtration and washed with 2:1 acetonitrile/water (3×1 mL) to afford 317 mg (61%) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated to 50° C. for 5 h
  2. stirringAfter stirring the mixture for 2 h
  3. filtrationthe solid was collected by filtration
  4. washwashed with 2:1 acetonitrile/water (3×1 mL)

Sources & evidence

ORD record
ord-41569efb36284549a33e200ea2966f74
Source dataset
uspto-grants-2010_06
Patent number
US07732465B2

Linked notes

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