N-Iodosuccinimide → [1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

HRID 2036656노트

반응식

HRID 2036656 반응식
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[CH:21]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:23]N1C(=O)CCC1=O>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1[I:23])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 120273N-IodosuccinimideHCID 67433032(1-Imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester

생성물 1

HCID 67433097[1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of (1-imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester (2.5 g, 8.44 mmol) in acetonitrile (30 mL) was added N-iodosuccinimide (2.3 g, 10.13 mmol) at rt and stirred overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-5% MeOH in DCM to provide [1-(3-iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester: LC-MS (ESI) m/z 422.9 [M+H]+.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-4538b214207f46c39db986138874f505
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575183B2

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