N-(5-[2-Bromo-5-(4-methyl-piperazine-1-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide → N-(4-methyl-5-{5-[(4-methylpiperazin-1-yl)sulfonyl]-3-thienyl}-1,3-thiazol-2-yl)acetamide

HRID 1948424노트

반응식

HRID 1948424 반응식
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC>C1COCC1>[CH3:16][C:8]1[N:9]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[S:11][C:7]=1[C:6]1[CH:5]=[C:4]([S:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)(=[O:19])=[O:18])[S:3][CH:2]=1

참가 물질

4

반응물 2

HCID 86623148N-(5-[2-Bromo-5-(4-methyl-piperazine-1-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamideHCID 178418339Butyllithium

생성물 1

HCID 11998679N-(4-methyl-5-{5-[(4-methylpiperazin-1-yl)sulfonyl]-3-thienyl}-1,3-thiazol-2-yl)acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

N-{5-[2-Bromo-5-(4-methyl-piperazine-1-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (400 mg; 0.83 mmol; 1 eq), is dissolved in anhydrous THF (50 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (4.2 ml; 1.6 M; 6.67 mmol; 8 eq) is added dropwise. After 1 hour the reaction is complete and quenched with water. Solvents are evaporated and the crude product is dissolved in EtOAc. The resulting organic phase is washed with water (2 times), brine and dried over MgSO4. After evaporation of the solvents, the resulting product is precipitated in an ether/DCM mixture, affording Compound (29) as a white-off solid (125 mg; 37%).

후처리

  1. customquenched with water
  2. customSolvents are evaporated
  3. dissolutionthe crude product is dissolved in EtOAc
  4. washThe resulting organic phase is washed with water (2 times), brine
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents
  7. customthe resulting product is precipitated in an ether/DCM mixture

출처 및 근거

ORD 기록
ord-e60fffba3dec4c48ae19e1fe3270e7bf
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399497B2

반응 노트

불러오는 중…