N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide → HCID 11993497, compound

HRID 1364495Notes

Reaction equation

HRID 1364495 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 11993497HCID 11993497, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c868110c6c2941c7a04cf7e885390f77
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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