4-Methylmorpholine → HCID 68988679、化合物

HRID 2381480ノート

反応式

HRID 2381480 の反応式
[Br:1][CH:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3](Cl)=[O:4].CN1CCOCC1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[NH2:25]>O1CCCC1>[Br:1][CH:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([NH:25][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][N:19]=1)=[O:4]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 78747AminopyrazineHCID 866351792-Bromo-3-cyclopentyl-propionyl chloride

生成物 1

HCID 68988679HCID 68988679、化合物収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-bromo-3-cyclopentyl-propionyl chloride (1.46 g, 6.09 mmol) in tetrahydrofuran (32.1 mL, 0.19M) cooled to 0° C. was treated with N-methylmorpholine (0.66 mL, 6.09 mmol). The reaction mixture was stirred at 0° C. for 5 min. After this time, the reaction was treated with pyrazin-2-ylamine (0.58 g, 6.09 mmol) and allowed to warm to 25° C. The reaction stirred at 25° C. for 2 d. After this time, the reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×150 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (AnaLogix, 115 g, 10-50% ethyl acetate/hexanes gradient) afforded 2-bromo-3-cyclopentyl-N-pyrazin-2-yl-propionamide (0.43 g, 24%) as a light brown solid; ES+-HRMS m/e calcd for C12H16N3OBr [M+H+] 298.0550, found 298.0550.

後処理

  1. temperatureto warm to 25° C
  2. stirringThe reaction stirred at 25° C. for 2 d
  3. customAfter this time, the reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×150 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6364eb04cb1e4a3fa064e0862e68e25d
出典データセット
uspto-grants-2012_09
特許番号
US08258134B2

反応ノート

読み込み中…