Tetrahydrofuran → 5-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine

HRID 78188Notes

Reaction equation

O1CCCC1.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1)#[CH:7].[O:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[N:30][OH:31])=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O>[O:15]([C:22]1[N:23]=[CH:24][C:25]([CH2:28][C:29]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=3)[O:31][N:30]=2)=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (2 mL) solution of 5-ethynyl-pyridin-2-ylamine (30 mg, 0.25 mmol) described in Manufacturing Example 28-1-3 were added (2-phenoxy-pyridin-5-yl)-acetohydroximoyl chloride (100 mg, 0.381 mmol) described in Manufacturing Example 40-1-4 and triethylamine (70.8 μL, 0.508 mmol), which was stirred for 8 hours at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (26 mg, 30%).

Workup

extractionwhich was extracted with ethyl acetate
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-fa32d548c8e749ad8364f01b482e1c8b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Reaction notes

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