4-Toluenesulfonyl chloride → 2-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate

HRID 1792457노트

반응식

HRID 1792457 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH:10]([OH:13])[C:11]#[N:12])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:13][CH:10]([C:11]#[N:12])[CH2:9][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 220313423-(5-Bromo-2-pyridinylamino)-2-hydroxypropionitrile

생성물 1

HCID 235374122-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate수율 64.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7.2 g of 3-(5-bromo-2-pyridinylamino)-2-hydroxypropionitrile was dissolved in 60 mL dichloromethane, and 7.8 mL diisopropyl ethylamine and 6.3 g of 4-toluenesulfonic acid chloride were added thereto, and while the temperature of the mixture was gradually increased to room temperature, the mixture was stirred for 2 hours. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture which was then extracted with ethyl acetate and washed with brine, then the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give 7.64 g of the title compound (yellow oil).

후처리

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0dbdc9783d4d489ab198e2f789e8084b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074801B1

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