Lawesson's reagent → (R)-2-(Benzo[1,3]dioxol-5-yloxy)-5-fluoro-N-[2-fluoro-4-(1-thiocarbamoyl-ethoxy)-benzyl]-nicotinamide

HRID 350990Notes

Reaction equation

HRID 350990 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[N:33]=[CH:32][C:31]([F:34])=[CH:30][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C@@H:24]([C:26](=O)[NH2:27])[CH3:25])=[CH:19][C:18]=3[F:29])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[N:33]=[CH:32][C:31]([F:34])=[CH:30][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C@@H:24]([C:26](=[S:44])[NH2:27])[CH3:25])=[CH:19][C:18]=3[F:29])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10162322(R)-2-(Benzo[1,3]dioxol-5-yloxy)-N-[4-(1-carbamoyl-ethoxy)-2-fluoro-benzyl]-5-fluoro-nicotinamide

Product 1

HCID 60128050(R)-2-(Benzo[1,3]dioxol-5-yloxy)-5-fluoro-N-[2-fluoro-4-(1-thiocarbamoyl-ethoxy)-benzyl]-nicotinamideYield 163.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-2-(benzo[1,3]dioxol-5-yloxy)-N-[4-(1-carbamoyl-ethoxy)-2-fluoro-benzyl]-5-fluoro-nicotinamide (1.0 g, 2.12 mmol) and Lawesson's reagent (0.52 g, 1.27 mmol) in dry tetrahydrofuran (10 ml) was stirred at room temperature 2 h. The solvent was removed in vacuo. The residue was adsorbed onto silica gel and purified by column chromatography (20% ethyl acetate/hexane) to afford 1.01 g of a yellow solid (98% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4c963a97fe504ac8b9bff654cf683205
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

Loading…