Ammonium Chloride → (S)-N-((S)-1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

HRID 2170321노트

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HRID 2170321 반응식
[Br:1][C:2]1[C:3]([CH:10]=[N:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([F:28])[CH:27]=1)[CH2:22][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[C:3]([C@H:10]([NH:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:22][C:21]2[CH:20]=[C:19]([F:18])[CH:27]=[C:26]([F:28])[CH:25]=2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[Br:1][C:2]1[C:3]([C@@H:10]([NH:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:22][C:21]2[CH:20]=[C:19]([F:18])[CH:27]=[C:26]([F:28])[CH:25]=2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 90280277(S)-N-((5-bromo-2-(methylthio)pyrimidin-4-yl)methylene)-2-methylpropane-2-sulfinamideHCID 178505920HCID 178505920, 화합물

생성물 2

HCID 90311859(S)-N-((S)-1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamideHCID 90312182(S)-N-((R)-1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of (S)—N-((5-bromo-2-(methylthio)pyrimidin-4-yl)methylene)-2-methylpropane-2-sulfinamide (11C, 2.97 g. 8.8 mmol) in THF (18 mL) cooled to −78° C. was drop wise added 3,5-difluorobenzylmagnesium bromide (53 mL, 0.25 M in Ether, 13.3 mmol). After stirring at −78° C. for 10 min, NH4Cl (sat. aq.) (10 ml) was added to the reaction and warmed up to ambient temperature. Extracted with EtOAc and the organic layer was dried with Na2SO4(s). The solvent was removed and the residue was purified by flash column to yield the title compound (11E) and (S)—N—((S)-1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (11D). MS (m/z) 465.87 [M+H]+

후처리

  1. temperaturewarmed up to ambient temperature
  2. extractionExtracted with EtOAc
  3. dry with materialthe organic layer was dried with Na2SO4(s)
  4. customThe solvent was removed
  5. customthe residue was purified by flash column

출처 및 근거

ORD 기록
ord-97b9b5562a724434b1cef4ba996c0ca4
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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