Triethylamine → HCID 53628651、化合物

HRID 1260224ノート

反応式

HRID 1260224 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:25][CH2:26][CH2:27][CH2:28]OS(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C>CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:28][CH2:27][CH2:26][F:25])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonate2 回HCID 57470074HCID 57470074、化合物

生成物 1

HCID 53628651HCID 53628651、化合物収率 45.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

0.215 g of 4-isopropyl-N-[4-((S)-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.0.62 mmol) and 0.16 g of toluene-4-sulfonic acid 3-fluoro-propyl ester (0.69 mmol) were dissolved in 5 ml of dimethylformamide, 0.43 ml of triethylamine added and the reaction stirred for 1 h at 50° C. Additional toluene-4-sulfonic acid 3-fluoro-propyl ester and triethylamine were added to drive the reaction to completion. After stirring at room temperature for 15 h, the solvent was evaporated, the residue re-dissolved in dichloromethane, and the organic layer washed with 1 N aqueous sodium hydroxide. The aqueous phase was extracted twice with dichloromethane, the organic layers combined, dried over magnesium sulfate, filtered and the solvent evaporated. The crude product was purified via silica gel chromatography (chromabond column) using dichloromethane/methanol 0-3%. Fractions containing the product were collected and the solvent evaporated to yield 0.115 g of the desired product.

後処理

  1. customthe reaction to completion
  2. stirringAfter stirring at room temperature for 15 h
  3. customthe solvent was evaporated
  4. dissolutionthe residue re-dissolved in dichloromethane
  5. washthe organic layer washed with 1 N aqueous sodium hydroxide
  6. extractionThe aqueous phase was extracted twice with dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThe crude product was purified via silica gel chromatography (chromabond column)
  11. additionFractions containing the product
  12. customwere collected
  13. customthe solvent evaporated

出典と根拠

ORDレコード
ord-74d3f94dd9534cc8bfd966331565caa9
出典データセット
uspto-grants-2013_06
特許番号
US08470810B2

反応ノート

読み込み中…