N-Iodosuccinimide → 7-Cyclobutyl-5-iodo-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 244130ノート

反応式

HRID 244130 の反応式
[CH:1]1([C:5]2[N:13]3[C:8]([C:9](=[O:14])[NH:10][CH:11]=[N:12]3)=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[I:15]N1C(=O)CCC1=O>CN(C=O)C>[CH:1]1([C:5]2[N:13]3[C:8]([C:9](=[O:14])[NH:10][CH:11]=[N:12]3)=[C:7]([I:15])[N:6]=2)[CH2:2][CH2:3][CH2:4]1

参加物

4

反応物 2

HCID 120273N-Iodosuccinimide2 回HCID 1359932727-cyclobutyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

生成物 1

HCID 1360179687-Cyclobutyl-5-iodo-3H-imidazo[5,1-f][1,2,4]triazin-4-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

A solution of 7-cyclobutyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one (789 mg, 4.15 mmol) and N-iodosuccinimide (933 mg, 4:15 mmol) in anhydrous DMF (40 mL) was stirred overnight at rt. An additional 4 equiv of NIS was added and reaction was heated to 55° C. for 6 h. The reaction mixture was concentrated in vacuo and partitioned between DCM and H2O and separated. The aqueous layer was washed with DCM (3×) and the combined organic fractions were washed with 1M sodium thiosulfate (Na2S2O3) (IX), brine (1×), dried over sodium sulfate (Na2SO4), filtered, and concentrated in vacuo. The solid was triturated with 20% EtOAc in DCM and filtered through a fritted Buchner funnel resulting in the title compound as an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 1.84-1.96 (m, 1H), 1.98-2.13 (m, 1H), 2.25-2.43 (m, 4H), 3.84-3.96 (m, 1H), 7.87 (s, 1H); MS (ES+): m/z 317.02 (100) [MH+], HPLC: tR=2.62 min (MicromassZQ, polar—5 min).

後処理

  1. customreaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between DCM and H2O
  4. customseparated
  5. washThe aqueous layer was washed with DCM (3×)
  6. washthe combined organic fractions were washed with 1M sodium thiosulfate (Na2S2O3) (IX), brine (1×)
  7. dry with materialdried over sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe solid was triturated with 20% EtOAc in DCM
  11. filtrationfiltered through a fritted Buchner funnel

出典と根拠

ORDレコード
ord-d44c5b54138d41c4a2241c12c62ba3aa
出典データセット
uspto-grants-2014_02
特許番号
US08653268B2

反応ノート

読み込み中…