Sodium hydride → (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one

HRID 2204547노트

반응식

HRID 2204547 반응식
[CH:1]1([C:7](=[O:17])[CH2:8]P(=O)(OCC)OCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[S:20]([N:30]1[C:34]2=[N:35][CH:36]=[C:37]([CH:39]=O)[N:38]=[C:33]2[CH:32]=[CH:31]1)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH:1]1([C:7](=[O:17])/[CH:8]=[CH:39]/[C:37]2[N:38]=[C:33]3[CH:32]=[CH:31][N:30]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[C:34]3=[N:35][CH:36]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11043558Diethyl (2-cyclohexyl-2-oxoethyl)phosphonateHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

생성물 1

HCID 58010004(E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one수율 76.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of diethyl 2-cyclohexyl-2-oxoethylphosphonate (0.609 g, 2.32 mmol) in THF (10 mL) was added NaH (60% dispersion in mineral oil, 0.0664 g, 1.66 mmol). After about 30 min, a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (0.20 g, 0.64 mmol, Example#10, Step B) in THF (10 mL) was added. After about 2 h, EtOAc (50 mL) and saturated aqueous NH4Cl (50 mL) was added to the reaction mixture. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with IPA (20 mL) to provide (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one as a tan solid (0.20 g, 73%): LC/MS (Table 2, Method a) Rt=3.06 min; MS m/z: 410 (M+H)+.

후처리

  1. waitAfter about 2 h
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with IPA (20 mL)

출처 및 근거

ORD 기록
ord-b17be2d74e0449428e09d443fbbd4e2e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365579B2

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