Water → HCID 54739192, compound

HRID 2046294Notes

Reaction equation

[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([O:16]CC)=O)=[C:10]([OH:19])[C:9]([CH:20]([CH3:22])[CH3:21])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCN2C(=[N:27]CCC2)CC1.O.CC[O:37][C:38]([CH3:40])=[O:39]>O1CCOCC1>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:27][CH2:40][C:38]([OH:37])=[O:39])=[O:16])=[C:10]([OH:19])[C:9]([CH:20]([CH3:21])[CH3:22])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 130 °C

Procedure

Ethyl 2-cyclohexyl-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. DBU (0.06 mL, 0.398 mmol) was added to a solution of the compound from example 98b) (92 mg, 0.260 mmol) in 1,4-dioxane (1.5 ml) at room temperature. The reaction was heated in the microwave at 130° C. for 20 minutes. The reaction was cooled and H2O and EtOAc were added. The layers were separated and the aqueous phase backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The product was purified by column chromatography (SiO2, 10-20% EtOAc/Hexanes) to give the title compound as a colorless oil (36 mg, 45%). 1H NMR (400 MHz, DMSO-d6) d ppm 12.06 (s, 1H) 4.66 (tt, J=11.37, 4.04 Hz, 1H) 4.26 (q, J=7.07 Hz, 2H) 3.15 (sept, J=6.78 Hz, 1H) 1.51-1.89 (m, 7H) 1.29-1.44 (m, 2H) 1.26 (t, J=7.07 Hz, 3H) 1.16 (d, J=6.82 Hz, 6H) 1.08-1.22 (m, 1H).

Workup

temperatureThe reaction was cooled
customThe layers were separated
washThe combined organic layers were washed with Brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe product was purified by column chromatography (SiO2, 10-20% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-6b81b110337b43c99ce3dfaa00598140
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE044613E1

Reaction notes

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