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

HRID 538310ノート

反応式

HRID 538310 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ee3ce59f5eac4d529d93fb2c75438022
出典データセット
uspto-grants-2014_10
特許番号
US08865712B2

反応ノート

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