Triethylamine → N-{5-[5-({[2-(Dimethylamino)ethyl]amino}sulfonyl)-2-thienyl]-4-methyl-1,3-thiazol-2-YL}acetamide

HRID 1948395노트

반응식

HRID 1948395 반응식
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 66053N,N-Dimethylethylenediamine2회HCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

생성물 1

HCID 11998303N-{5-[5-({[2-(Dimethylamino)ethyl]amino}sulfonyl)-2-thienyl]-4-methyl-1,3-thiazol-2-YL}acetamide수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (1000 mg; 2.97 mmol; 1 eq) is dissolved in anhydrous DCM (100 ml). The reaction is put under nitrogen. 2-Dimethylaminoethylamine (0.97 ml; 8.91 mmol; 3 eq), triethylamine (1.66 ml; 11.9 mmol; 4 eq) are added successively and the reaction mixture is stirred overnight at room temperature. After 15 hours, to complete the reaction, triethylamine (4 eq) and 2-dimethylaminoethylamine (3 eq) are added. After one hour the reaction is complete. The reaction mixture is then wash with NH4Cl sat. (twice) and brine. The organic layer is dried over MgSO4 and the solvents are evaporated. The resulting crude product is dissolved in DCM and extracted with HCl 1N. The aqueous phase is washed with DCM (3 times) and basified with NaOH 5N until pH 10. The desired product is extracted with EtOAc (3 times). Combined organic phases are dried over MgSO4, filtrated and evaporated, affording Compound (3) as a beige solid (480 mg; 40%).

후처리

  1. waitAfter 15 hours
  2. additionare added
  3. waitAfter one hour the reaction is complete
  4. washThe reaction mixture is then wash with NH4Cl sat. (twice) and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvents are evaporated
  7. dissolutionThe resulting crude product is dissolved in DCM
  8. extractionextracted with HCl 1N
  9. washThe aqueous phase is washed with DCM (3 times)
  10. extractionThe desired product is extracted with EtOAc (3 times)
  11. dry with materialCombined organic phases are dried over MgSO4
  12. filtrationfiltrated
  13. customevaporated

출처 및 근거

ORD 기록
ord-7a3b97f83848449a8e689e6cce22d5e9
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399497B2

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