Lawesson's reagent → 5-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-thioxo-morpholin-3-yl)-pyridin-2-yl]-amide

HRID 538310Notes

Reaction equation

HRID 538310 reaction equation
[F:1][CH2:2][C:3]1([C:10]2[N:15]=[C:14]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][CH2:6][C:5](=O)[NH:4]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1COCC1>[F:1][CH2:2][C:3]1([C:10]2[N:15]=[C:14]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][CH2:6][C:5](=[S:35])[NH:4]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 866680245-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-oxo-morpholin-3-yl)-pyridin-2-yl]-amide

Product 1

HCID 866680255-Chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-thioxo-morpholin-3-yl)-pyridin-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-pyridine-2-carboxylic acid [6-(3-fluoromethyl-5-oxo-morpholin-3-yl)-pyridin-2-yl]-amide (0.24 g, 0.658 mmol) in THF (10.0 ml), Lawesson's reagent (0.798 g, 1.974 mmol) was added at rt and heated at reflux temperature for 24 h. Reaction mass was concentrated under reduced pressure. The crude compound was directly purified by column chromatography using 23% ethyl acetate in hexane to furnish title compound as off-white solid. Yield=0.19 g (72% [2 steps]). TLC (50% ethyl acetate in hexane) Rf=0.71; LCMS: RtH8=1.578, [M+1]+=381.1 and 382.9.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 24 h
  3. customReaction mass
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude compound was directly purified by column chromatography

Sources & evidence

ORD record
ord-ee3ce59f5eac4d529d93fb2c75438022
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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