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

HRID 1246425노트

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HRID 1246425 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-99c6ee4e506344cea1d4dbac51bc2821
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125901B2

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