Ammonium Hydroxide → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid amide

HRID 1958077Notes

Reaction equation

[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:17]=[N:16][C:15]([C:18](O)=[O:19])=[CH:14][CH:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].C(N1C=CN=C1)([N:24]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:17]=[N:16][C:15]([C:18]([NH2:24])=[O:19])=[CH:14][CH:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (100 mg, 0.31 mmol) in DMF (5 mL) was added 1,1′-carbonyldiimidazole (60 mg, 0.37 mmol). The resulting reaction mixture was stirred for 1 h at 60° C. and then treated with an ammonium hydroxide solution (476 μL, 3.1 mmol). After 2 h the reaction mixture was evaporated and purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (49 mg, 55%) as an off white solid. MS: m/e=313.2 [M+Na]+.

Workup

customThe resulting reaction mixture
customAfter 2 h the reaction mixture was evaporated
custompurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-877d437f0a414bdcb57b57da7f0c9ccb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410104B2

Reaction notes

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