Water → 2-[5-Bromo-6-oxo-4-{[(1r,2r,3r,5s)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]oxy}pyridazin-1(6h)-yl]-n-(pyridin-4-ylmethyl)acetamide

HRID 2092124

Reaction equation

Br[C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[C:6](=[O:9])[C:7]=1[Br:8].[CH3:21][CH:22]1[CH:30]([OH:31])[CH2:29][CH:25]2[C:26]([CH3:28])([CH3:27])[CH:23]1[CH2:24]2.[H-].[Na+].O>O1CCOCC1>[Br:8][C:7]1[C:6](=[O:9])[N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[N:4]=[CH:3][C:2]=1[O:31][C@@H:30]1[CH2:29][C@@H:25]2[CH2:24][C@@H:23]([C:26]2([CH3:28])[CH3:27])[C@H:22]1[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To 2-(4,5-dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide (50 mg, 0.124 mmol) and (1R,2R,3R,5S)-(−)-isopinocampheol (50 mg, 0.324 mmol) in 1,4-dioxane (2 mL), sodium hydride (15 mg, 0.313 mmol) was added at 0° C., and stirred at 100° C. for 5 days. After completion of the reaction, the reaction mixture was mixed with water and extracted with chloroform and ethyl acetate. The combined organic layer was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (1.7 mg, 3% yield).

Workup

customAfter completion of the reaction
extractionextracted with chloroform and ethyl acetate
customThe combined organic layer was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-c56953d6b35a44e2a5f9e7b82d1c8e60
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440666B2

Linked notes

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