Water → tert-butyl 2-[6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl]hydrazinecarboxylate

HRID 469193Notes

Reaction equation

[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].Cl[C:11]1[N:12]=[N:13][C:14]([C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[CH:15][CH:16]=1.O.C(=O)([O-])O.[Na+]>C(O)CCC.C(OC(=O)C)C>[CH3:22][N:20]1[CH:21]=[C:17]([C:14]2[N:13]=[N:12][C:11]([NH:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[CH:16][CH:15]=2)[CH:18]=[N:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-butyl carbazate, 8.98 g (67.3 mmol) and 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine (11.9 g, 61.1 mmol) were mixed in 1-butanol (245 mL). This mixture was heated till 90° C. and stirred at that temperature for 16 h. The reaction mixture was cooled and water (250 mL) and ethylacetate (250 mL) were added. The biphasic mixture was neutralised with sodium hydrogencarbonate till the pH is 7. Then the organic layer was separated and the water layer was extracted with ethylacetate (250 mL). The combined organic layers were washed once with water (250 mL) and evaporated. The residue was stirred in isopropylether, filtered off and dried under vacuum. Yield: 5.9 g (20.3 mmol; 33%) of the title compound.

Workup

temperatureThe reaction mixture was cooled
customThen the organic layer was separated
extractionthe water layer was extracted with ethylacetate (250 mL)
washThe combined organic layers were washed once with water (250 mL)
customevaporated
stirringThe residue was stirred in isopropylether
filtrationfiltered off
customdried under vacuum

Sources & evidence

ORD record: ord-8bdeb6c41d014b839912adece49a875b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629144B2

Reaction notes

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