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 549968ノート

反応式

HRID 549968 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 866312444-(4-formyl-2-thiazolyl)-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidineHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

生成物 1

HCID 866420471-[4-(4-Ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-55e313b2339944349d0483e57e11a4cd
出典データセット
uspto-grants-2011_05
特許番号
US07943774B2

反応ノート

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