Allylamine → HCID 178456915、化合物

HRID 1620493ノート

反応式

HRID 1620493 の反応式
S=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.[CH2:8]([NH2:11])[CH:9]=[CH2:10].S(C1C=CC(C)=CC=1)(O)(=O)=O.[F:23][C:24]([F:45])([F:44])[C:25]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH:34]=O)[CH2:30][CH2:29]1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)C>[F:23][C:24]([F:45])([F:44])[C:25]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][CH:31](/[CH:34]=[C:6]2/[C:2]([NH:11][CH2:8][CH:9]=[CH2:10])=[N:3][C:4](=[O:7])[S:5]/2)[CH2:30][CH2:29]1

参加物

7

反応物 5

HCID 7853AllylamineHCID 25517Ammonium ChlorideHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 23665647Potassium tert-butoxideHCID 866786841-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate

生成物 1

HCID 178456915HCID 178456915、化合物収率 44.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4-thioxo-1,3-thiazolidin-2-one (60 mg) in ethanol (2 mL) was added prop-2-en-1-amine (26 mg) at room temperature. The reaction mixture was stirred at room temperature for 2 hr. 1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate (230 mg) and potassium tert-butoxide (101 mg) were added to the reaction mixture at room temperature, and the mixture was stirred at 80° C. for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (95 mg).

後処理

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-5a519cf2e9ee42e0af5572da4f41a196
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

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