Water → HCID 67384784, compound

HRID 77243Notes

Reaction equation

HRID 77243 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:10][N:9]=1.[CH2:25]([OH:34])[CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][OH:33].O>CN(C=O)C>[OH:34][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8172Triethylene GlycolHCID 11430Potassium CarbonateHCID 59217426HCID 59217426, compound

Product 1

HCID 67384784HCID 67384784, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of potassium carbonate (158.7 mg, 1.15 mmol), compound 3 (100 mg, 0.38 mmol) and triethylene glycol (576 mg, 3.8 mmol) in anhydrous DMF (5.0 ml) was sealed in a microwavable vial (from Biotage) and subjected to microwave irradiation (Biotage Initiator system) at 180° C. for 25 min. After cooling to room temperature, water was added and reaction mixture was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified with PTLC (4% MeOH in DCM as developing solvent) gave product 7 (110 mg, Yield: 77%): 1H NMR (200 MHz, CDCl3): δ.8.20 (3H, m), 7.83 (1H, d, d, J1=8.6 Hz, J2=2.4 Hz), 7.61 (2H, d, J=8.8 Hz), 7.10 (2H, m) 6.84 (1H, d, J=8.6 Hz), 4.53 (2H, t, J=4.8 Hz), 3.88 (2H, t, J=4.8 Hz), 3.71 (6H, m), 3.61 (2H, m), 2.10 (1H, b), HRMS (EI) m/z calcd. for [C19H22N2O6]+ 374.1478.

Workup

  1. customwas sealed in a microwavable vial (from Biotage)
  2. customsubjected to microwave irradiation (Biotage Initiator system) at 180° C. for 25 min
  3. customreaction mixture
  4. extractionwas extracted with ethyl acetate
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customThe residue was purified with PTLC (4% MeOH in DCM as developing solvent)

Sources & evidence

ORD record
ord-6dba23df5a464aa9a16367a646c4cb50
Source dataset
uspto-grants-2014_09
Patent number
US08840866B2

Reaction notes

Loading…