Ethyl vinyl ether → 1-(1-ethoxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-amine

HRID 1615704Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][NH:12][C:13]=2[NH:14]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([O:20][CH:21]=[CH2:22])[CH3:19]>C(Cl)Cl.O1CCOCC1>[CH2:18]([O:20][CH:21]([N:12]1[C:13]([NH2:14])=[C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=[N:11]1)[CH3:22])[CH3:19]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide (17.6 g, 78 mmol), ethoxyethene (11.2 mL, 117 mmol) and HO in 1,4-dioxane (1 mL, 4 mmol) in CH2Cl2 (520 mL) was stirred at room temperature for 1 h and concentrated in vacuo. The residue was dissolved in ethanol (260 mL) and 25% aq. NaOH solution (260 mL) and the reaction mixture was heated to 75° C. for 4 h and cooled to room temperature. The ethanol was partly concentrated in vacuo and the resulting solid collected by filtration, washed with water and minimum cold ethanol and dried in vacuo to provide the title compound as a solid (16 g).

Workup

concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in ethanol (260 mL)
temperaturecooled to room temperature
concentrationThe ethanol was partly concentrated in vacuo
filtrationthe resulting solid collected by filtration
washwashed with water and minimum cold ethanol
customdried in vacuo

Sources & evidence

ORD record: ord-afa75d7cf15c4814945104fc3221a326
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765762B2

Reaction notes

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