Hydrazine hydrate (1:1) → {2-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-pyridin-4-yl}-hydrazine

HRID 60666Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 67a (633 mg, 2.62 mmol) was suspended in EtOH (5 mL) and hydrazine hydrate (50-60%, 5 mL) in a microwave vial fitted with a stirrer bar and sealed with a crimped septum, and heated to 80° C. for 18 h. The reaction was cooled, and partitioned between H2O and EtOAc. The organic layer was separated, and the aqueous extracted again with EtOAc. The combined organics were dried over MgSO4, and concentrated in vacuo to afford the title compound as a colorless oil (593 mg, 89%). LCMS (Method 3) Rt 0.41 and 1.71 min, m/z 276.2 [M+Na].

Workup

customsealed with a crimped septum
temperatureThe reaction was cooled
custompartitioned between H2O and EtOAc
customThe organic layer was separated
extractionthe aqueous extracted again with EtOAc
dry with materialThe combined organics were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9b75eef4e17740bfa0e7e9cea924f8d1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440974B2

Reaction notes

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