Tetrahydrofuran → 9-{[4-(1-Methylethyl)phenoxy]methyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1622643노트

반응식

HRID 1622643 반응식
[CH3:1][CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH3:3].C1COCC1.[H-].[Na+].Cl[CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30]>O>[CH3:3][CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]2[C:11]3=[N:16][S:29](=[O:31])(=[O:30])[CH2:28][CH2:27][N:12]3[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH3:1]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 150356783-{[4-(1-Methylethyl)phenoxy]methyl}pyridin-2-amine

생성물 1

HCID 668240069-{[4-(1-Methylethyl)phenoxy]methyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide수율 36.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 3-{[4-(1-methylethyl)phenoxy]methyl}pyridin-2-amine (600 mg) and dehydrated THF (10 ml) was added to a mixture of sodium hydride (60%, 495 mg), 2-chloroethanesulfonyl chloride (1211 mg) and dehydrated THF (10 ml) at room temperature. The reaction mixture was stirred for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (methanol/ethyl acetate) to give the title compound (303 mg) as a white solid. The obtained solid was crystallized from THF-diisopropyl ether to give a white solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-c2a20c20e19741bb9fd30868de3e84f7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778934B2

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