6-Methoxypyridazin-3-amine → HCID 117925948, compound

HRID 594130

Reaction equation

HRID 594130 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:14]([CH3:28])[O:13][N:12]=1>N1C=CC=CC=1>[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH:9][C:6]3[N:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[C:14]([CH3:28])[O:13][N:12]=1

Participants

4

Reactant 2

HCID 816736-Methoxypyridazin-3-amineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride

Product 1

HCID 117925948HCID 117925948, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-methoxypyridazin-3-amine (125 mg, 1.0 mmol) in pyridine (8 mL) at room temperature, was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (0.302 g, 1.0 mmol). The reaction mixture was stirred at 20° C. for 18 hours. The solvent was evaporated in vacuo and passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol, followed by a sulphonic acid (SCX) SPE cartridge eluting with methanol. The crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-25% methanol gradient), to provide the title compound (16 mg). LCMS (2 min, formic) Rt 0.83 min, m/z (ES+) 391 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionpassed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
  3. washeluting with methanol
  4. washeluting with methanol
  5. customThe crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-25% methanol gradient)

Sources & evidence

ORD record
ord-a6f100bcc13f4355b07a0d68d4972464
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Linked notes

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