Triethylamine → 3-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amine

HRID 870705노트

반응식

HRID 870705 반응식
[Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.[C:19]([O:23][CH2:24][CH2:25][NH2:26])([CH3:22])([CH3:21])[CH3:20]>C(O)(C)C.C(OCC)(=O)C>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:26][CH2:25][CH2:24][O:23][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 219146142-(Tert-butoxy)ethanamineHCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazine

생성물 1

HCID 866964073-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amine수율 2.6%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (216 mg, 1.0 mmol), triethyl amine (0.35 mL, 2.5 mmol) and 2-(tert-butoxy)ethanamine (180 mg, 1.5 mmol) in isopropanol (2 mL) was heated at 65° C. for overnight. The mixture was cooled, diluted with ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to give brown solid as crude in quantitative yield for further synthesis. 20 mg was further purified by Prep HPLC to give pure 3-bromo-N-(2-(tert-butoxy)ethyl)imidazo[1,2-b]pyridazin-6-amine as white solid (8 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.57 (d, J=9.85 Hz, 1H), 7.42 (s, 1H), 6.76 (d, J=9.60 Hz, 1H), 4.56 (s, 1H), 3.67 (t, J=5.94 Hz, 2H), 3.53 (t, J=5.94 Hz, 2H), 1.24 (s, 9H) LRMS (ESI) m/e 315.0 [(M+H)+, calcd for C12H18BrN4O 314.2].

후처리

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give brown solid as crude in quantitative yield
  6. customfor further synthesis
  7. custom20 mg was further purified by Prep HPLC

출처 및 근거

ORD 기록
ord-58ce1a2c39fd41d7bf81420f3adb7e21
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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