Pyridine → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(4-morpholinyl)-3-pyridinyl]benzenesulfonamide

HRID 594129

Reaction equation

[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.[CH3:15][C:16]1[C:20]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[C:19]([CH3:33])[O:18][N:17]=1.N1C=CC=CC=1>ClCCl>[CH3:15][C:16]1[C:20]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([S:29]([NH:8][C:7]3[C:2]([CH3:1])=[N:3][C:4]([N:9]4[CH2:14][CH2:13][O:12][CH2:11][CH2:10]4)=[CH:5][CH:6]=3)(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[C:19]([CH3:33])[O:18][N:17]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-methyl-6-(4-morpholinyl)-3-pyridinamine (170 mg, 0.880 mmol) and 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (265 mg, 0.880 mmol) in dichloromethane (4 mL) and pyridine (0.142 mL, 1.759 mmol) was heated at 65° C. for 2 hours. The reaction mixture was allowed to cool and separated between dichloromethane and saturated sodium bicarbonate solution. The organic phase was passed through a hydrophobic frit and evaporated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient) to give the title compound (271 mg) as an off-white solid. LCMS (2 min, formic) Rt 0.82 min, m/z (ES+) 459 (M+H).

Workup

temperatureto cool
customseparated between dichloromethane and saturated sodium bicarbonate solution
customevaporated in vacuo
customThe crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)

Sources & evidence

ORD record: ord-75a9d3df05874e72a0adbffa52cd92ee
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Linked notes

Loading…