2-Amino-5-cyanopyridine → N-(5-cyanopyridin-2-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)benzenesulfonamide

HRID 594133Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 6-amino-3-pyridinecarbonitrile (30 mg, 0.252 mmol) in pyridine (1 mL) at room temperature, was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (84 mg, 0.277 mmol). The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand overnight. The solvent was evaporated in vacuo. The sample was purified by passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol, followed by a sulphonic acid (SCX) SPE cartridge eluting with methanol then 2M ammonia/methanol. The product-containing fractions were concentrated to give the title compound (23 mg) as an off-white solid. LCMS (2 min, formic) Rt 0.88 min, m/z (ES+) 385 (M+H)

Workup

waitleft
waitto stand overnight
customThe solvent was evaporated in vacuo
customThe sample was purified
extractionby passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
washeluting with methanol
washeluting with methanol
concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record: ord-913bb42f3d6d44d9bb1c149ffb43fad2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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