Hydrazine hydrate (1:1) → HCID 66966126, compound

HRID 1054210Notes

Reaction equation

N1C=CC=C([C:7]([C:9]2[C:10]([C:15](OC)=O)=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])C=1.O.[NH2:20][NH2:21]>C(O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:9][C:10]=1[C:15]1[C:10]2[N:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:7](=[O:8])[NH:21][N:20]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of methyl 3-picolinoylpicolinate 7, (240 mg, 0.99 mmol), hydrazine hydrate (63 μL, 1.3 mmol) and 12 mL of absolute ethanol was heated to 75° C. in a sealed tube for 1 h. After cooling, the solid was collected by vacuum filtration and dried under air suction. The mother liquor was concentrated to dryness under reduced pressure and purified by normal phase flash chromatography eluting with 0-10% methanol in dichloromethane over approximately 20 minutes. Like fractions were combined and concentrated under reduced pressure and combined with the solid collected by filtration to give 8-(pyridin-2-yl)pyrido[2,3-d]pyridazin-5(6H)-one 9 (150 mg, 0.67 mmol). 1H NMR (400 MHz, Methanol-d4) δ 9.07 (dd, J=4.5, 1.6 Hz, 1H), 8.98 (dd, J=8.4, 1.6 Hz, 1H), 8.72 (ddd, J=4.9, 1.7, 1.0 Hz, 1H), 8.00 (ddd, J=7.9, 7.3, 1.7 Hz, 1H), 7.99-7.92 (m, 1H), 7.97-7.84 (m, 1H), 7.53 (ddd, J=7.3, 4.9, 1.5 Hz, 1H). LCMS: (M+H)+, 225.

Workup

temperatureAfter cooling
filtrationthe solid was collected by vacuum filtration
customdried under air suction
concentrationThe mother liquor was concentrated to dryness under reduced pressure
custompurified by normal phase flash chromatography
washeluting with 0-10% methanol in dichloromethane over approximately 20 minutes
concentrationconcentrated under reduced pressure
filtrationcollected by filtration

Sources & evidence

ORD record: ord-f0c70623359e47cfa39c730c9c1d5cc0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394299B2

Reaction notes

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