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

HRID 1360857ノート

反応式

HRID 1360857 の反応式
[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]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 66053N,N-Dimethylethylenediamine2 回HCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4f467f456561411198c904e176adc0d6
出典データセット
uspto-grants-2011_02
特許番号
US07879888B2

反応ノート

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