Tetrahydrofuran → HCID 59255194, compound

HRID 1693973Notes

Reaction equation

O1CCCC1.[CH:6]1([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19](Cl)=[N:20][OH:21])=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:23]([C:25]1[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=1)#[CH:24].C(N(CC)CC)C>O>[CH:6]1([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[CH:24]=[C:23]([C:25]4[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=4)[O:21][N:20]=3)=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (3 mL) solution of (4-cyclopentyloxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.592 mmol) described in Manufacturing Example 78-1-4 and 3-ethynyl-pyridin-2-ylamine described in Manufacturing Example 1-2-3 (45 mg, 0.378 mmol) was added triethylamine (206 μL, 1.48 mmol), which was stirred for 3 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and 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 (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (44 mg, 22%).

Workup

extractionwhich was then extracted with ethyl acetate
washThe organic layer was washed with water and 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 (heptane:ethyl acetate=4:1-2:1)

Sources & evidence

ORD record: ord-a33bfa26bf99412abc2aa75d8ee41ee4
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158657B2

Reaction notes

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