Hydrazine → 1-(3-fluoro-5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyridin-2-yl)hydrazine

HRID 219282Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:10]=[N:11][N:12]([CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:13]=2)=[CH:4][N:3]=1.[NH2:23][NH2:24]>CC(O)C.O>[F:8][C:7]1[C:2]([NH:23][NH2:24])=[N:3][CH:4]=[C:5]([C:9]2[CH:10]=[N:11][N:12]([CH2:14][CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH:13]=2)[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2,3-difluoro-5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyridine (3.0 g, 9.5 mmol) in IPA (47.7 mL, 0.2 M) at room temperature was added hydrazine (3.6 mL, 114.4 mmol). The reaction mixture was stirred at 60° C. for 2 h, at which point the reaction was cooled to room temperature and concentrated in vacuo. The concentrated material was suspended in saturated NaHCO3 solution and filtered to obtain product as a white, fluffy solid. The material was re-suspended in water (30 mL), filtered, and dried under high vacuum to obtain 1-(3-fluoro-5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyridin-2-yl)hydrazine (2.2 g, 72% yield) as an orange solid. MS m/z=322.2 [M+1]+. Calc'd for C15H20FN5O2: 321.4.

Workup

temperaturewas cooled to room temperature
concentrationconcentrated in vacuo
filtrationfiltered
customto obtain product as a white, fluffy solid
filtrationfiltered
customdried under high vacuum

Sources & evidence

ORD record: ord-4188ee317fd540ce90cb52cedcfd1a19
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Reaction notes

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