Water → HCID 11999020、化合物

HRID 1948450ノート

反応式

HRID 1948450 の反応式
[CH2:1]([NH:4][S:5]([C:8]1[S:12][C:11](Br)=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C([Li])CCC.O>C1COCC1>[CH2:1]([NH:4][S:5]([C:8]1[S:12][CH:11]=[C:10]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])[CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 962WaterHCID 86623160N-(5-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamideHCID 178418339Butyllithium

生成物 1

HCID 11999020HCID 11999020、化合物収率 10%

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-{5-[(allylamino)sulfonyl]-2-bromo-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide obtained in Step I as described above (35 mg; 0.08 mmol; 1 eq), is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.18 ml; 1 M; 0.18 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 1 hour before being hydrolyzed with water (0.3 ml). Reaction is warmed up to room temperature before being concentrated to dryness. Residue is taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Title compound is purified by reverse preparative HPLC, affording Compound (49) as a white powder (3 mg; 10%).

後処理

  1. customreaction
  2. customReaction
  3. temperatureis warmed up to room temperature
  4. concentrationbefore being concentrated to dryness
  5. customThe organic phases are decanted
  6. dry with materialdried over MgSO4
  7. filtrationfiltrated
  8. customevaporated
  9. customTitle compound is purified by reverse preparative HPLC

出典と根拠

ORDレコード
ord-ce9274d6530945c18375dd8a8201c8ab
出典データセット
uspto-grants-2013_03
特許番号
US08399497B2

反応ノート

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