Pyridazine → HCID 67466849, compound

HRID 2202794Notes

Reaction equation

C([Li])CCC.CC1(C)CCCC(C)(C)N1.[C:16]([O:20][C:21]([N:23]1[CH:28]2[CH2:29][CH2:30][CH:24]1[CH2:25][C:26](=[O:31])[CH2:27]2)=[O:22])([CH3:19])([CH3:18])[CH3:17].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1.[Cl-].[NH4+]>C1COCC1>[C:16]([O:20][C:21]([N:23]1[CH:28]2[CH2:29][CH2:30][CH:24]1[CH2:25][C:26]([OH:31])([C:37]1[N:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH2:27]2)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyl lithium (1.8 mL, 4.5 mmol) was added to a solution of 2,2,6,6-tetramethylpiperidine (0.76 mL, 4.5 mmol) in THF (25 mL) at −30° C., warmed to 0° C. and stirred for 30 minutes. After cooling to −78° C., a solution of 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.675 g, 3.0 mmol) and pyridazine (0.29 mL, 4. mmol) in THF (5 mL) was added dropwise and stirred for 1 hour. A solution of saturated aqueous ammonium chloride was added and the mixture extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 60-100% ethyl acetate/cyclohexane. The fractions containing the two desired products were concentrated under vacuum to give the title compounds.

Workup

temperatureAfter cooling to −78° C.
stirringstirred for 1 hour
extractionthe mixture extracted into ethyl acetate
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent removed by evaporation under vacuum
customThe residue was purified by flash chromatography on silica eluting with 60-100% ethyl acetate/cyclohexane
additionThe fractions containing the two desired products
concentrationwere concentrated under vacuum

Sources & evidence

ORD record: ord-59bd2742ce3c4397bb1ba17425e7ac91
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365564B2

Reaction notes

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