Hydrochloric Acid → N-(4-(2-(4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl)ethyl)-1,3-thiazol-2-yl)acetamide

HRID 1246425ノート

反応式

HRID 1246425 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.CS[C:21]1[S:22][CH2:23][CH2:24][N:25]=1.Cl>>[S:22]1[CH2:23][CH2:24][N:25]=[C:21]1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

生成物 1

HCID 21915298N-(4-(2-(4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl)ethyl)-1,3-thiazol-2-yl)acetamide収率 20.3%

反応条件

温度
120 °C

実験手順

N-(4-(2-(4-Aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (1.8 g) prepared in a similar manner according to Step 6 of Production Example 1, 2-(methylsulfanyl)-4,5-dihydro-1,3-thiazole (918 mg), hydrochloric acid concentrate (0.57 ml) and 2-methoxyethanol (28 ml) were combined under nitrogen atmosphere, and stirred at 120° C. for 10 hours. After cooled to room temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in tetrahydrofuran/water, and made basic with aqueous potassium carbonate. The mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash column chromatography over silica gel with chloroform/methanol (30:1→20:1) as an eluent, and triturated with ethyl acetate to give N-(4-(2-(4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl)ethyl)-1,3-thiazol-2-yl)acetamide (484.7 mg) as an off-white solid.

後処理

  1. concentrationconcentrate (0.57 ml) and 2-methoxyethanol (28 ml)
  2. temperatureAfter cooled to room temperature
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in tetrahydrofuran/water
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography over silica gel with chloroform/methanol (30:1→20:1) as an eluent
  9. customtriturated with ethyl acetate

出典と根拠

ORDレコード
ord-99c6ee4e506344cea1d4dbac51bc2821
出典データセット
uspto-grants-2006_10
特許番号
US07125901B2

反応ノート

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