Trifluoroacetic acid → 3-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine

HRID 706848노트

반응식

HRID 706848 반응식
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[C:15][C:16]2[N:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][CH:17]=2)[CH2:9]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:18]1[CH:17]=[C:16]([C:15]#[C:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[N:20]2[C:19]=1[CH:24]=[CH:23][CH:22]=[N:21]2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 867095651-BOC-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine

생성물 1

HCID 867095663-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine수율 121.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-BOC-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)piperidine (0.39 g, 1.2 mmol) in CH2Cl2 (10 mL) was added TFA (1.23 g, 10.8 mmol), the mixture was stirred at rt overnight and evaporated in vacuo. To the residue was added 10 mL 10% K2CO3 solution, extracted with EtOAc (20 mL×3), dried with Na2SO4, after filtration, and the filtrate was evaporated under reduced pressure to give 0.33 g product as yellow oil (107.0%). 1H NMR (300 MHz, CDCl3) δ: 8.43 (1 H, d, J=4.5 Hz), 7.93-7.97 (1 H, dd, J=1.8 and 9.0 Hz), 7.91 (1 H, s), 7.05-7.09 (1 H, dd, J=4.5 and 9.0 Hz), 2.82-2.98 (4 H, m), 2.08-2.11 (1 H, m), 1.75-1.84 (2 H, m), 1.53-1.58 (2 H, m).

후처리

  1. customevaporated in vacuo
  2. additionTo the residue was added 10 mL 10% K2CO3 solution
  3. extractionextracted with EtOAc (20 mL×3)
  4. dry with materialdried with Na2SO4
  5. filtrationafter filtration
  6. customthe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-226936f991934786888d4488629699f9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174996B2

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