Potassium Carbonate → 1'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]-2,3-dihydrospiro[indene-1,4'-piperidine]

HRID 2036071노트

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HRID 2036071 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.Cl.[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:15]3[CH2:20][CH2:19][C:18]4([C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[CH2:17][CH2:16]3)=[CH:7][CH:6]=2)[S:12][N:11]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 109218293-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazineHCID 225093272,3-Dihydrospiro[indene-1,4'-piperidine] hydrochloride

생성물 1

HCID 866399981'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]-2,3-dihydrospiro[indene-1,4'-piperidine]수율 60.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

3-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazine (51 mg), 2,3-dihydrospiro[indene-1,4′-piperidine] hydrochloride (78 mg) and potassium carbonate (70 mg) were suspended in N,N-dimethylformamide (3 mL), and the suspension was stirred at 80° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed twice with aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane to 50% ethyl acetate/hexane) and recrystallized from hexane/ethyl acetate to give the object product (53 mg, 60%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed twice with aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane to 50% ethyl acetate/hexane)
  6. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-4e0355b16b984d69b678132c3e425198
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575167B2

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