Pyridine → HCID 89876288, compound

HRID 594128

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[N:6][C:7]=1[CH3:8].N1C=CC=CC=1.[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[C:25]([CH3:39])[O:24][N:23]=1>ClCCl>[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([NH:1][C:2]3[C:7]([CH3:8])=[N:6][C:5]([N:9]4[CH2:13][CH2:12][O:11][C:10]4=[O:14])=[CH:4][CH:3]=3)(=[O:37])=[O:36])=[CH:33][CH:34]=2)=[C:25]([CH3:39])[O:24][N:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 3-(5-amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one (80 mg, 0.414 mmol) in dichloromethane (3 mL) and pyridine (0.033 mL, 0.414 mmol) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (125 mg, 0.414 mmol). The reaction vessel was sealed and heated at 65° C. for 6 hours. The reaction mixture was then allowed to cool and separated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL). The organic phase was separated using a hydrophobic frit and evaporated in vacuo. The crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (137 mg) as a colourless glassy solid. LCMS (2 min, formic) Rt 0.92 min, m/z (ES+) 459 (M+H).

Workup

customThe reaction vessel was sealed
temperatureto cool
customseparated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL)
customThe organic phase was separated
customevaporated in vacuo
customThe crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)
customevaporated in vacuo

Sources & evidence

ORD record: ord-6df9302049dd4f26b955ab67804c55e5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Linked notes

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