Tetrahydrofuran → 2-Methyl-5-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridine

HRID 78199

Reaction equation

O1CCCC1.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[N:12][CH:13]=1)#[CH:7].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[N:31][OH:32])=[CH:25][CH:24]=1.C(N(CC)CC)C>O>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[O:32][N:31]=[C:30]([CH2:29][C:26]3[CH:25]=[CH:24][C:23]([CH2:22][O:21][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=4)=[CH:28][CH:27]=3)[CH:7]=2)=[CH:13][N:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (2 mL) solution of 5-ethynyl-2-methyl-pyridine (10 mg, 85 mmol) described in Manufacturing Example 190-1-1 were added 4-(pyridin-2-yloxymethyl)-phenyl-acetohydroximoyl chloride (31 mg, 0.11 mmol) described in Manufacturing Example 2-1-5 and triethylamine (18 μL, 0.13 mmol), which was stirred for 2 hours and 30 minutes at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrated was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (14 mg, 46%).

Workup

extractionwhich was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrated was concentrated under a reduced pressure
customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-10f27dd646a84988b9be58d038ab64e7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Linked notes

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