4-Methylmorpholine → 3-((4-Bromo-1H-pyrazol-1-yl)methyl)benzamide

HRID 2175253노트

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HRID 2175253 반응식
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11](O)=[O:12])[CH:6]=1.C[N:18]1CCOCC1.ClC(OCC(C)C)=O.[OH-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([NH2:18])=[O:12])[CH:6]=1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 6610343-((4-bromo-1H-pyrazol-1-yl)methyl)benzoic acid

생성물 1

HCID 470613323-((4-Bromo-1H-pyrazol-1-yl)methyl)benzamide수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzoic acid (0.20 g, 0.711 mmol) in THF (3.5 mL) at 0° C. was added N-methylmorpholine (0.086 g, 0.854 mmol), and isobutyl chloroformate (0.107 g, 0.783 mmol) slowly. The reaction was stirred at 0° C. for 1.5 h and ammonium hydroxide (0.249 g, 7.11 mmol) was slowly added. The reaction was allowed to warm to room temperature where it stirred overnight. At the conclusion of this period, the reaction mixture was partitioned between DCM and water. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.188 g, 94%). LCMS, [M+H]+=280.0.

후처리

  1. temperatureto warm to room temperature where it
  2. stirringstirred overnight
  3. customAt the conclusion of this period, the reaction mixture was partitioned between DCM and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-767b103b6242468989ffc202027855be
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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