Dimethylformamide → N-picolyl piperidine sulfonamide

HRID 842244ノート

反応式

HRID 842244 の反応式
N1C=CC=CC=1CN1CCC([S:18]([N:21]2[CH2:26][CH2:25][CH:24](OC3C=CC(OC(F)(F)F)=CC=3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])(C(OC)=O)CC1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52]Cl.C[N:55](C)C=O>>[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52][NH:55][S:18]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)(=[O:19])=[O:20]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 22052615Methyl 1-(2-pyridinylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate

生成物 1

HCID 30666388N-picolyl piperidine sulfonamide収率 72%

反応条件

温度
35 °C

実験手順

Part I: Preparation of methyl 1-(2-pyridinylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. The unsubstituted piperidine sulfonamide from part H (7.9 g, 16.95 mmol) was dissolved in dry dimethylformamide (35 mL) and potassium carbonate (7.05 g, 51.1 mmol) and 2-picolyl chloride hydrochloride (4.21 g, 25.67 mmol) were added. The reaction was stirred at 35° C. for sixteen hr and then concentrated in vacuo. The residue was taken up in ethyl acetate and filtered through Celite. The filtrate washed with water two times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) provided the N-picolyl piperidine sulfonamide as a white solid (6.8 g, 72%).

後処理

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered through Celite
  3. washThe filtrate washed with water two times, saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ce267b546c104d41880163c34c3b0832
出典データセット
uspto-grants-2002_04
特許番号
US06372758B1

反応ノート

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