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

HRID 1360902ノート

反応式

HRID 1360902 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-40f5067d4a6b4a18901b170a2a092ed6
出典データセット
uspto-grants-2011_02
特許番号
US07879888B2

反応ノート

読み込み中…