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

HRID 2036071Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-4e0355b16b984d69b678132c3e425198
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575167B2

Reaction notes

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