Hydrazine → [3,5-Difluoro-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine

HRID 1391433Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([F:15])=[C:4]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[NH2:25][NH2:26]>O1CCOCC1>[F:8][C:7]1[C:2]([NH:25][NH2:26])=[N:3][C:4]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[C:5]([F:15])[C:6]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[2,3,5-Trifluoro-6-(2-morpholin-4-yl-ethoxy)-pyridin-4-yl]-morpholine (1.2 g; 3.5 mmol) and hydrazine (2 g) were added to dioxane (10 mL) and heated to 100° C. for six hours. The solvent was evaporated, and the residue was dissolved in dichloromethane (20 mL) and washed with a 10% sodium carbonate solution (2 mL). It was dried over magnesium sulfate, and evaporated, to give crude [3,5-Difluoro-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine. The crude product was then dissolved in ethanol. To the solution was added one drop of acetic acid, and m-tolylaldehyde (600 mL; 5 mmol) and it was heated at 60° C. overnight. The solvent was then evaporated, and the residue was purified by column chromatography to give Compound 12 (850 mg). Theoretical Mass Ion: 461.1; observed MH+ peak: 462.1.

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in dichloromethane (20 mL)
washwashed with a 10% sodium carbonate solution (2 mL)
dry with materialIt was dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-eef168c0494848bfbc245c2a3df23d0d
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338951B2

Reaction notes

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