2,3-Dichloro-5-(trifluoromethyl)pyridine → HCID 11511722, compound

HRID 2422118Notes

Reaction equation

HRID 2422118 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:6](=[O:22])[N:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[S:8](=[O:17])(=[O:16])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:24]1[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[CH:26][N:25]=1>CN(C=O)C>[C:18]([N:7]1[C:6](=[O:22])[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:24]2[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:34])([F:32])[F:33])=[CH:26][N:25]=2)=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8]1(=[O:17])=[O:16])([CH3:19])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 67244954HCID 67244954, compound

Product 1

HCID 11511722HCID 11511722, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-[(2-Aminoethyl)amino]-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.088 g, 0.27 mmol), 2,3-dichloro-5-(trifluoromethyl)pyridine (0.065 g, 0.30 mmol) and TEA (0.055 g, 0.54 mmol) was dissolved in dry DMF (3 ml) and heated in a microwave reactor at 120° C. for 25 mins. The reaction mixture was extracted with EtOAc (75 ml) and the organic phases were washed with water (3×50 ml), dried over MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography using petroleum ether and EtOAc (85:15) as eluant, to give the title compound (0.052 g, 38%). 1H NMR (500 MHz, CDCl3): δ 8.3-8.25 (m, 1H), 7.67-7.62 (m, 2H), 7.49-7.43 (m, 2H), 7.43-7.35 (m, 3H), 6.47-6.41 (m, 1H), 5.47-5.41 (m, 1H), 3.52 (q, 2H), 3.09 (q, 2H), 1.7 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 159.4, 155.7, 143.7, 143.6, 135.5, 133.2, 133.1, 131.5, 129.4, 128.5, 125, 124.6, 122.4, 116.8, 116.6, 115, 107.1, 61.4, 45.4, 40.9, 27.5; Mass Spectrum: M−H+ 503.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (75 ml)
  2. washthe organic phases were washed with water (3×50 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-951a9204d3ed4df6a93ff0776d0a1188
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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