Triethylamine → HCID 178441253, compound

HRID 76306Notes

Reaction equation

HRID 76306 reaction equation
[CH2:1]([C:5]1[C:9](=[NH:10])[S:8][N:7]([C:11]([CH3:15])([CH3:14])[CH2:12][F:13])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:19]=1[C:20](Cl)=[O:21].C(N(CC)CC)C>C1COCC1>[CH2:1]([C:5]1=[CH:6][N:7]([C:11]([CH3:14])([CH3:15])[CH2:12][F:13])[S:8]/[C:9]/1=[N:10]\[C:20](=[O:21])[C:19]1[CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=[CH:26][C:18]=1[O:17][CH3:16])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15571508HCID 15571508, compoundHCID 66867922HCID 66867922, compound

Product 1

HCID 178441253HCID 178441253, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 152C (0.46 g, 2.0 mmol) in THF (10 mL) were added 2-methoxy-5-(trifluoromethyl)benzoyl chloride (0.52 g, 2.2 mmol, JRD Fluorochemicals Ltd) and triethylamine (0.84 mL, 6.0 mmol). After stirring at 60° C. for 14 hr, the reaction mixture was cooled to room temperature, quenched with saturated NaHCO3 (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% ethyl acetate in dichloromethane) to afford 75 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.3 Hz, 3 H), 1.22-1.46 (m, 2 H), 1.65 (s, 2 H), 1.65 (s, 6 H), 2.63-2.83 (m, 2 H), 3.89 (s, 3 H), 4.60 (d, J=47.1 Hz, 2 H), 7.31 (d, J=8.8 Hz, 1 H), 7.80 (dd, J=8.6, 2.5 Hz, 1 H), 8.10 (d, J=2.4 Hz, 1 H), 8.63 (s, 1 H); MS (ESI+) m/z 433 (M+H)+; Anal. Calculated C20H24F4N2O2S: C, 55.54; H, 5.59; N, 6.48. Found: C, 55.75; H, 5.23; N, 6.43.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customquenched with saturated NaHCO3 (10 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b0037230f42b464699ba0e8b64e23116
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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