Imidazole → 4-Chloro-2-(2-imidazol-1-yl-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927516Notes

Reaction equation

HRID 1927516 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:33])[C:13]2[O:19][C:18]3[C:20]([Cl:29])=[CH:21][C:22]([NH:24][C:25](=[O:28])[CH2:26]Cl)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:30])[C:14]=2[CH:32]=1)=[O:9]>CN(C=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:33])[C:13]2[O:19][C:18]3[C:20]([Cl:29])=[CH:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:30])[C:14]=2[CH:32]=1)=[O:9]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284974-Chloro-2-(2-imidazol-1-yl-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Imidazole (0.215 g, 3.16 mmol) was added to a solution of Example 133 (0.7 g, 1.58 mmol) in DMF (15 mL) and the reaction mixture was stirred at 120° C. for 2.5 h. It was concentrated, treated with water and the solid that precipitated was filtered, washed with water and purified using flash chromatography (silica gel, 4% methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.4 g, (53.33%); 1H NMR (DMSO-d6): δ 2.66 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 4.97 (s, 2H, CH2), 5.4 (s, 2H, CH2), 6.9 (s, 1H, Ar), 7.2 (s, 1H, Ar), 7.64 (s, 1H, Ar), 7.7 (d, 1H, Ar), 7.9 (d, 1H, Ar), 8.12 (s, 1H, Ar), 8.2 (s, 1H, Ar), 10.72 (bs, 1H, NH); MS: m/e (ES+) 476 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. custompurified

Sources & evidence

ORD record
ord-cdf27d5884884969bd55e1b367641801
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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