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

HRID 1172481Notes

Reaction equation

HRID 1172481 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]([CH3:32])[C:13]2[O:19][C:18]3[C:20]([Cl:28])=[CH:21][C:22]([NH:24][CH2:25][CH2:26]Cl)=[CH:23][C:17]=3[CH2:16][S:15](=[O:30])(=[O:29])[C:14]=2[CH:31]=1)=[O:9]>CN(C=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:32])[C:13]2[O:19][C:18]3[C:20]([Cl:28])=[CH:21][C:22]([NH:24][CH2:25][CH2:26][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:29])(=[O:30])[C:14]=2[CH:31]=1)=[O:9]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 1317284464-Chloro-2-(2-chloro-ethylamino)-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 1317284514-Chloro-2-(2-imidazol-1-yl-ethylamino)-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
110 °C

Procedure

Imidazole (0.118 g, 1.73 mmol) was added in an atmosphere of nitrogen, to a solution of Example 56k (1.3 g, 2.63 mmol) in dry DMF (10 mL) with stirring. The reaction mixture was then maintained at 110° C. for 18 h. It was cooled, concentrated and the solid obtained was filtered washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.120 g, (22.38%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.2 (t, 2H, CH2), 3.9 (s, 3H, OCH3), 4.1 (t, 2H, CH2), 5.2 (s, 2H, CH2), 6.4 (s, 1H, NH), 6.6 (s, 1H, Ar), 6.75 (s, 1H, Ar), 6.9 (s, 1H, Ar), 7.2 (s, 1H, Ar), 7.6 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.2 (s, 1H, Ar); MS: m/e (ES+) 462 (M+).

Workup

  1. temperatureIt was cooled
  2. concentrationconcentrated
  3. customthe solid obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-addc886a70f14176a0eccd349507dfa9
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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