Triethylamine → 1-(2-Methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

HRID 549244Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][C:7]([C:17]([NH2:19])=O)=[N:6]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][C:7]([C:17]#[N:19])=[N:6]1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 9845Trifluoroacetic anhydride

HCID 671581031-(2-methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide

Product 1

HCID 671574891-(2-Methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrileYield 99.8%

Procedure

The method described in Part F of Example 3 was used to treat 1-(2-methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide (3.41 g, 12.7 mmol) with trifluoroacetic anhydride (1.98 mL, 14.0 mmol) in the presence of triethylamine (3.86 g, 38.1 mmol) with the following modifications. Extractions were carried out four times with chloroform, and the automated flash chromatography column was eluted with ethyl acetate. 1-(2-Methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile (3.16 g) was obtained as a colorless oil.

Workup

extractionExtractions
washthe automated flash chromatography column was eluted with ethyl acetate

Sources & evidence

ORD record: ord-0373cf3ec72b421687e5dd6069b056e8
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943636B2

Reaction notes

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