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 1364495노트

반응식

HRID 1364495 반응식
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]

참가 물질

4

반응물 1

HCID 136052757N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide2회

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c868110c6c2941c7a04cf7e885390f77
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888379B2

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