Hydrazine hydrate (1:1) → HCID 90427508, compound

HRID 718177Notes

Reaction equation

[CH2:1]([C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)[CH:11]=2)=[CH:7][CH:6]=[C:5](F)[N:4]=1)[CH3:2].O.[NH2:24][NH2:25].C([O-])(O)=O.[Na+]>CC(O)C>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=3)[CH:11]=2)=[CH:7][CH:6]=[C:5]([NH:24][NH2:25])[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Ethyl-6-fluoro-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (0.15 g, 0.51 mmol) was suspended in 2-propanol (1.0 mL) in a screw-cap reaction vessel. Hydrazine hydrate (0.12 mL, 2.5 mmol) was added, the reaction vessel was sealed and the mixture was stirred at 90° C. for 18 h. Sat. NaHCO3 (aq) (20 mL) was added and the mixture was extracted wth EtOAc (4×35 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 2-ethyl-6-hydrazinyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (0.15 g, 96%) as a light yellow solid that was used in the next step without further purification. MS (ESI) m/z: 311.2 (M+H+).

Workup

customthe reaction vessel was sealed
extractionthe mixture was extracted wth EtOAc (4×35 mL)
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-154ea21b522e4bb2b0e6b0cbb13aea7e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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