Lawesson's reagent → HCID 178480327, compound

HRID 82768Notes

Reaction equation

HRID 82768 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=O)[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[O:22][CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2[CH3:29])/[N:7]([CH2:31][C@H:32]2[CH2:36][CH2:35][CH2:34][O:33]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[O:22][CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2[CH3:29])=[S:46])/[N:7]([CH2:31][C@H:32]2[CH2:36][CH2:35][CH2:34][O:33]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178480326HCID 178480326, compound

Product 1

HCID 178480327HCID 178480327, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of Example 24 (300 mg, 0.571 mmol) in toluene (6 mL) at ambient temperature was added Lawesson's Reagent (231 mg, 0.571 mmol). This mixture was warmed to 95° C. and allowed to stir for 4 hours. The mixture was then cooled to ambient temperature, concentrated under reduced pressure. The residue was dissolved in EtOAc (20 mL) and washed with NaHCO3 solution. The organics were combined, dried, concentrated, and the residue was purified by Analogix® Intelliflash280™ (SiO2, 0-10% (7 M ammonia in methanol) in CH2Cl2 over 25 min) to obtain the title compound in 87% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.37 (s, 9 H) 1.47-1.63 (m, 4 H) 1.73-1.89 (m, 4 H) 2.10 (q, J=8.59 Hz, 1 H) 2.19 (s, 3 H) 2.38-2.47 (m, 1 H) 2.81-2.90 (m, 1 H) 3.59-3.67 (m, 1 H) 3.71-3.81 (m, 1 H) 3.96 (ddd, J=14.67, 9.41, 5.76 Hz, 2 H) 4.27-4.34 (m, 3 H) 7.23 (d, J=8.82 Hz, 1 H) 7.55-7.59 (m, 2 H) 7.63 (dd, J=8.82, 2.03 Hz, 1 H); MS (DCI/NH3) m/z 542 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washwashed with NaHCO3 solution
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by Analogix® Intelliflash280™ (SiO2, 0-10% (7 M ammonia in methanol) in CH2Cl2 over 25 min)

Sources & evidence

ORD record
ord-5e86c3c3378d492a9c6264a93adca722
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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