Lawesson's reagent → HCID 90402242, compound

HRID 576718Notes

Reaction equation

HRID 576718 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Cl:23][C:24]1[C:39]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:37]=[CH:36][C:25]=1[CH2:26][N:27]1[C@@H:32]([CH3:33])[CH2:31][NH:30][C:29](=O)[C:28]1=[O:35]>C1COCC1>[Cl:23][C:24]1[C:39]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:37]=[CH:36][C:25]=1[CH2:26][N:27]1[C@@H:32]([CH3:33])[CH2:31][NH:30][C:29](=[S:10])[C:28]1=[O:35]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 90402638HCID 90402638, compound

Product 1

HCID 90402242HCID 90402242, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a heterogeneous mixture of Lawesson's reagent (650 mg, 1.6 mmol) in THF (30 mL) was added Intermediate 4 (1.0 g, 3.1 mmol) in one portion. The mixture was heated at 55° C. for 20 minutes and then concentrated to remove solvent. Purification by chromatography (SiO2; hexanes—100% EtOAc) afforded the desired product as a yellow solid (950 mg, 90%). MS (ESI): mass calcd. for C13H12ClF3N2OS, 336.0; m/z found, 337.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.78 (d, J=4.2 Hz, 1H), 7.65 (d, J=7.9 Hz, 2H), 7.38 (t, J=7.8 Hz, 1H), 5.17 (d, J=15.6 Hz, 1H), 4.53 (d, J=15.6 Hz, 1H), 3.84-3.66 (m, 2H), 3.40 (dd, J=11.7, 5.6 Hz, 1H), 1.38 (d, J=6.7 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. customto remove solvent
  3. customPurification by chromatography (SiO2; hexanes—100% EtOAc)

Sources & evidence

ORD record
ord-b165d4f19f6842d29f007ed4147c0224
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

Loading…