Hydrochloric Acid → HCID 21914702, 화합물

HRID 1246509노트

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HRID 1246509 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:26][C:27](=[O:29])[CH3:28])[S:13][C:14]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.CS[C:32]1[S:33][CH2:34][CH2:35][N:36]=1.Cl.C([O-])(O)=O.[Na+]>COCCO>[S:33]1[CH2:34][CH2:35][N:36]=[C:32]1[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:26][C:27](=[O:29])[CH3:28])[S:13][C:14]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 516892Sodium BicarbonateHCID 21914845N-(4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl)acetamide

생성물 1

HCID 21914702HCID 21914702, 화합물수율 58.4%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

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온도
120 °C

실험 절차

A mixture of N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}-acetamide (200 mg), 2-(methylsulfanyl)-4,5-dihydro-1,3-thiazole (62 mg), concentrated HCl (0.064 ml) and 2-methoxyethanol (3 ml) was stirred at 120° C. for 13 hours under N2 atmosphere. After cooled to r.t., the reaction mixture was made basic with saturated NaHCO3. The mixture was extracted with AcOEt. The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by preparative silica gel chromatography with CHCl3/MeOH (10:1) as an eluent to give N-{4-{2-[4-(4,5-dihydro-1,3-thiazol-2-ylamino)phenyl]ethyl}-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (139.8 mg) as a pale yellow amorphous substance.

후처리

  1. temperatureAfter cooled to r.t.
  2. extractionThe mixture was extracted with AcOEt
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative silica gel chromatography with CHCl3/MeOH (10:1) as an eluent

출처 및 근거

ORD 기록
ord-5fe0962b202942d78d51b6145b462051
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125901B2

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