Potassium Carbonate → 1-[4-(4-Ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 549968Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([CH:21]=O)[N:20]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:23]([F:26])([F:25])[F:24])[CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:21]([C:19]1[N:20]=[C:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:23]([F:26])([F:24])[F:25])=[N:5]3)[CH2:15][CH2:14]2)[S:17][CH:18]=1)#[CH:27]

Participants

Conditions

Temperature: 40 °C

Procedure

Under argon, 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-carbaldehyde (200 mg) is dissolved in methanol (5 ml) and potassium carbonate (215 mg) and dimethyl 1-diazo-2-oxopropylphosphonate (199 mg) are added. The mixture is stirred at 40° C. After aqueous work-up, the mixture is extracted with ethyl acetate and the extracts are dried with sodium sulphate and concentrated under reduced pressure. The residue is purified chromatographically. This gives 1-[4-(4-ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (67 mg).

Workup

extractionAfter aqueous work-up, the mixture is extracted with ethyl acetate
dry with materialthe extracts are dried with sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue is purified chromatographically

Sources & evidence

ORD record: ord-55e313b2339944349d0483e57e11a4cd
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943774B2

Reaction notes

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