Potassium Carbonate → 1-{3-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl}-2-phenylpyrrolidine

HRID 521580

반응식

HRID 521580 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1.[C:12]1([CH:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[CH3:11][C:8]1[N:6]2[N:7]=[C:2]([N:19]3[CH2:20][CH2:21][CH2:22][CH:18]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2618922-PhenylpyrrolidineHCID 9113876-Chloro-3-methyl-(1,2,4)triazolo(4,3-b)pyridazine

생성물 1

HCID 711159701-{3-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl}-2-phenylpyrrolidine수율 12%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (200 mg, 1.19 mol), 2-phenylpyrrolidine (200 mg, 1.36 mmol) and K2CO3 (350 mg, 2.5 mmol) in acetonitrile (20 mL) was heated at 100° C. under microwave and stirred for 30 mins. After cooled to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuum. The residue was purified by prep-TLC (silica-gel, DCM: MeOH=20:1) to give product 3-methyl-6-(2-phenylpyrrolidin-1-yl)-[1,2,4]triazolo[4,3-b]pyridazine (Compound 10) as a white solid (30 mg, 12%). 1H NMR (300 MHz, CD3OD) δ 7.73-7.77 (d, 1H, J=10.2 Hz), 7.22-7.34 (m, 5H), 6.84-6.87 (d, 1H, J=10.2 Hz), 5.14-5.18 (m, 1H), 3.92-3.98 (m, 1H), 3.71-3.81 (m, 1H), 2.57 (s, 3H), 2.50-2.54 (M, 1H), 2.03-2.13 (m, 3H); LRMS (M+H+) m/z: calcd 279.15; found 279.

후처리

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate (20 mL*3)
  3. washThe combined organic layer was washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by prep-TLC (silica-gel, DCM: MeOH=20:1)

출처 및 근거

ORD 기록
ord-7c0bd7895aef4edd89798b32bf58533f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328117B2

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