Triethylamine → HCID 53628651, 화합물

HRID 1260224노트

반응식

HRID 1260224 반응식
[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]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonate2회HCID 57470074HCID 57470074, 화합물

생성물 1

HCID 53628651HCID 53628651, 화합물수율 45.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-74d3f94dd9534cc8bfd966331565caa9
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470810B2

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