p-Toluenesulfonic acid monohydrate → (R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

HRID 1432005노트

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HRID 1432005 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@H:13]([CH2:23][C:24]#[CH:25])[C:14]([NH:16][CH2:17][CH:18](OC)OC)=[O:15])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CC1C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:18]=[CH:17][NH:16][C:14](=[O:15])[C@H:13]2[CH2:23][C:24]#[CH:25])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86604868(R)-2-(3,4-dichlorobenzenesulfonamido)-N-(2,2-dimethoxyethyl)pent-4-ynamide

생성물 1

HCID 86604867(R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

A solution of (R)-2-(3,4-dichlorobenzenesulfonamido)-N-(2,2-dimethoxyethyl)pent-4-ynamide (36.7 g, 89.6 mmol) in 500 mL p-dioxane was treated with TsOH.H2O (5.11 g, 26.9 mmol). The reaction was heated to 60° C. for 7 h and then at 80° C. for 19 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with 400 mL EtOAc stirred with 400 mL 5% NaHCO3. The resulting precipitate was filtered and washed with H2O. The solid was suspended in hot EtOH and cooled to rt. The solid was collected by filtration, washed with EtOH and dried in vacuo to yield the title compound.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with 400 mL EtOAc
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with H2O
  6. temperaturecooled to rt
  7. filtrationThe solid was collected by filtration
  8. washwashed with EtOH
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-59642001d96a401590d92d9426a3b46d
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612060B2

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