Water → N-{4-methyl-5-[5-(morpholin-4-ylsulfonyl)-3-thienyl]-1,3-thiazol-2-yl}acetamide

HRID 1360902노트

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HRID 1360902 반응식
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][O:23][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.O>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][O:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])[S:3][CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 86623158N-{5-[2-bromo-5-(morpholin-4-ylsulfonyl)-3-thienyl]-4-methyl-1,3-thiazol-2-yl}acetamideHCID 178418339Butyllithium

생성물 1

HCID 11998911N-{4-methyl-5-[5-(morpholin-4-ylsulfonyl)-3-thienyl]-1,3-thiazol-2-yl}acetamide수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

N-{ 5-[2-bromo-5-(morpholin-4-ylsulfonyl)-3-thienyl]-4-methyl-1,3-thiazol-2-yl}acetamide (54 mg; 0.12 mmol; 1 eq) is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.16 ml; 1.6 M; 0.26 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 25 minutes before being hydrolyzed with water (0.3 ml). Crude material is warmed up to room temperature before being concentrated to dryness. Residue is then taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Crude material is purified by flash chromatography on silica gel using cyclohexane/EtOAc (10/90) as eluent, affording expected Compound (46) as an oil (30 mg; 67%).

후처리

  1. customreaction
  2. temperatureCrude material is warmed up to room temperature
  3. concentrationbefore being concentrated to dryness
  4. customThe organic phases are decanted
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. customevaporated
  8. customCrude material is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-40f5067d4a6b4a18901b170a2a092ed6
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879888B2

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