Tetrahydrofuran → HCID 44159841, compound

HRID 77937Notes

Reaction equation

O1CCCC1.[F:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[N:21][OH:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[C:26]([C:28]1[C:29]([NH2:34])=[N:30][CH:31]=[CH:32][CH:33]=1)#[CH:27].C(N(CC)CC)C>O>[F:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]4[C:29]([NH2:34])=[N:30][CH:31]=[CH:32][CH:33]=4)[O:22][N:21]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a tetrahydrofuran (10.0 mL) solution of (6-(4-fluoro-benzyloxy)-pyridin-3-yl)-acetohydroximoyl chloride (150 mg, 0.508 mmol) described in Manufacturing Example 58-1-5 and 3-ethynyl-pyridin-2-ylamine (30.0 mg, 0.254 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (106 μL, 0.762 mmol) at room temperature, which was stirred for 4 hours at 60° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:2) to obtain the title compound (21.2 mg, 22.2%).

Workup

extractionwhich was then extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:2)

Sources & evidence

ORD record: ord-7577968a0f1f484e86e67570804c3838
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Reaction notes

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