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

HRID 1364495ノート

反応式

HRID 1364495 の反応式
O[N:2]=[CH:3][C:4]1[S:8][C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])=[CH:6][CH:5]=1>N1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:3]([C:4]1[S:8][C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])=[CH:6][CH:5]=1)#[N:2]

参加物

4

反応物 1

HCID 136052757N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide2 回

生成物 1

HCID 11993497N-[5-(5-cyano-2-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 1049Pyridine溶媒

実験手順

N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide, Compound (14) (100 mg; 0.36 mmol; 1 eq.), is heated with copper acetate (3.3 mg; 0.018 mmol; 0.05 eq.) in neat pyridine (5 ml) at 75° C. for 1 hour. Reaction mixture is cooled down to room temperature and solvents are evaporated to dryness. The crude material is dissolved in dichloromethane, washed with water (10 ml) and dried over MgSO4. After evaporation of the solvents, the crude product is purified by flash chromatography using cyclohexane/ethyl acetate (90/10) as eluent. Compound (15) is obtained as a yellow powder (42 mg; 44%). 1H NMR (CDCl3, 300 MHz) δ 2.22 (s, 3H), 2.43 (s, 3H), 7.01 (d, J=6 Hz, 1H), 7.50 (d, J=6 Hz, 1H). M-(ESI): 262.3; M+(ESI): 264.3. HPLC, Rt: 3.03 min (purity: 91%).

後処理

  1. customReaction mixture
  2. customsolvents are evaporated to dryness
  3. dissolutionThe crude material is dissolved in dichloromethane
  4. washwashed with water (10 ml)
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents
  7. customthe crude product is purified by flash chromatography

出典と根拠

ORDレコード
ord-c868110c6c2941c7a04cf7e885390f77
出典データセット
uspto-grants-2011_02
特許番号
US07888379B2

反応ノート

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