Triethylamine → HCID 178495794, compound

HRID 78434Notes

Reaction equation

HRID 78434 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[S:7][C:6]1=[NH:12].CCN(CC)CC.[CH3:20][C:21]1([CH3:33])[CH2:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([C:30](Cl)=[O:31])[C:23]=2[O:22]1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[S:7]/[C:6]/1=[N:12]\[C:30]([C:29]1[C:23]2[O:22][C:21]([CH3:33])([CH3:20])[CH2:25][C:24]=2[CH:26]=[CH:27][CH:28]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27954702,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl chlorideHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495794HCID 178495794, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 126A (0.20 g, 1.1 mmol) and Et3N (0.45 mL, 3.2 mmol) in 30 mL THF was added 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl chloride (Acros, 0.34 g, 1.6 mmol). This mixture was warmed to reflux and allowed to stir for 2 hours. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The residue was diluted with 10 mL EtOAc and washed with 5 mL saturated, aqueous NH4Cl. The layers were separated and the aqueous layer was extracted 2×5 mL EtOAc. The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 4:1 hexanes:EtOAc) to provide the title compound (0.21 mmol, 0.57 mmol, 53% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.55 (s, 6H), 2.22 (s, 3H), 2.27 (s, 3H), 3.02 (s, 2H), 3.31 (s, 3H), 3.77-3.89 (m, 2H), 4.33-4.50 (m, 2H), 6.85 (t, J=7.5 Hz, 1H), 7.22 (d, J=7.5 Hz, 1H), 8.00 (d, J=8.1 Hz, 1H); MS (DCI/NH3) m/z 361 (M+H); Anal. calculated for C19H24N2O3S: C, 63.31; H, 6.71; N, 7.77. Found: C, 63.19; H, 6.50; N, 7.66.

Workup

  1. temperatureThis mixture was warmed
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with 10 mL EtOAc
  5. washwashed with 5 mL saturated
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted 2×5 mL EtOAc
  8. dry with materialThe combined organics were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. custompurified via flash column chromatography (SiO2, 4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-4d293541e8dc4353abbb130e15f30ff9
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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