Water → HCID 68874609, compound

HRID 490170Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[N:21]1[NH:22][C:23](=[O:27])[CH:24]=[CH:25][CH:26]=1.O>CN(C=O)C>[O:27]=[C:23]1[N:22]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[N:21]=[CH:26][CH:25]=[CH:24]1

Participants

Conditions

Temperature: 45 °C

Procedure

tert-Butyl 4-bromo-1-piperidinecarboxylate (1.00 g, 3.78 mmol) in DMF (20 mL) was treated with K2CO3 (523 mg, 3.78 mmol) and 3(2H)-pyridazinone (340 mg, 3.78 mmol) and then heated at 45° C. for 60 hours. The reaction mixture was allowed to cool to room temperature, poured into water (80 mL) and extracted with ethyl acetate (80 mL). The organic layer was washed with brine (3×50 mL), dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (elution with hexanes:ethyl acetate, 3:1) to provide the title compound (180 mg, 17% yield). 1H NMR (300 MHz, DMSO-d6) δ 1.41 (s, 9H), 1.66 (m, 4H), 2.91 (m, 2H), 4.05 (m, 2H), 4.96 (m, 1H), 6.93 (dd, 1H, J=1.5, 9.0 Hz), 7.39 (dd, 1H, J=3.0, 9.0 Hz), 7.95 (dd, 1H, J=3.0, 9.0 Hz); (MS (DCI/NH3) m/e 280 (M+H)+.

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate (80 mL)
washThe organic layer was washed with brine (3×50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (elution with hexanes:ethyl acetate, 3:1)

Sources & evidence

ORD record: ord-ed395862a6f542ef981f36e325e275a7
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528134B2

Reaction notes

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