Tetrahydrofuran → HCID 59255345, compound

HRID 1691151Notes

Reaction equation

[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](Cl)=[N:9][OH:10])[CH:2]=1.O1CCCC1.[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>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:24]=[C:23]([C:25]3[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=3)[O:10][N:9]=2)[CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of biphenyl-3-yl-acetohydroximoyl chloride (120 mg) described in Manufacturing Example 85-1-3 and tetrahydrofuran (6 mL) were added 3-ethynyl-pyridin-2-ylamine (28 mg, 0.24 mmol) described in Manufacturing Example 1-2-3 and triethylamine (200 μL, 1.4 mmol) at room temperature, which was stirred for 2.5 hours at 55° C. The reaction mixture was cooled to room temperature and water was added at that temperature, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (27 mg, 34%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
concentrationwas concentrated under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1)

Sources & evidence

ORD record: ord-86f8fc2a243b4f7e8b24814301e97462
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153662B2

Reaction notes

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