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

HRID 2175253ノート

反応式

HRID 2175253 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-767b103b6242468989ffc202027855be
出典データセット
uspto-grants-2015_06
特許番号
US09062028B2

反応ノート

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