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

HRID 870705ノート

反応式

HRID 870705 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-58ce1a2c39fd41d7bf81420f3adb7e21
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

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