Hydrazine hydrate (1:1) → HCID 90426581, compound

HRID 718134Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:4][CH:3]=1.O.[NH2:22][NH2:23]>CC(O)C>[NH:22]([C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:4][CH:3]=1)[NH2:23]

Participants

Conditions

Temperature: 80 °C

Procedure

4-((6-Fluoropyridin-3-yl)oxy)-2-(1-methyl-1H-pyrazol-4-yl)pyridine (0.99 g, 3.66 mmol) was dissolved in 2-propanol (7.3 mL) in a screw-cap reaction vessel. Hydrazine hydrate (64%) (0.9 mL, 18.3 mmol) was added, the vessel was sealed, and the reaction mixture was stirred at 80° C. for 12 h. The mixture was partitioned between sat. aqueous NaHCO3 (aq) (30 mL) and EtOAc (30 mL). The organic phase was collected and the aqueous phase was extracted with EtOAc (4×30 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 4-((6-hydrazinylpyridin-3-yl)oxy)-2-(1-methyl-1H-pyrazol-4-yl)pyridine (0.9 g, 87%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.29 (s, 1H), 8.33 (d, J=5.7 Hz, 1H), 8.23 (s, 1H), 8.00 (d, J=2.9 Hz, 1H), 7.93 (s, 1H), 7.48 (dd, J=9.0, 2.9 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 7.12 (d, J=9.0 Hz, 1H), 6.62 (dd, J=5.7, 2.4 Hz, 1H), 4.10 (d, J=4.5 Hz, 2H), 3.84 (s, 3H); MS (ESI) m/z: 283.1 (M+H+).

Workup

customthe vessel was sealed
customThe mixture was partitioned between sat. aqueous NaHCO3 (aq) (30 mL) and EtOAc (30 mL)
customThe organic phase was collected
extractionthe aqueous phase was extracted with EtOAc (4×30 mL)
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0061dc5cb24a4119b7db17803d4f7447
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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