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

HRID 1172533Notes

Reaction equation

HRID 1172533 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:28])[C:8]2[O:14][C:13]3[C:15]([Cl:24])=[CH:16][C:17]([NH:19][C:20](=[O:23])[CH2:21]Cl)=[CH:18][C:12]=3[CH2:11][S:10](=[O:26])(=[O:25])[C:9]=2[CH:27]=1)=[O:4].[CH3:29][NH:30][CH3:31].Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:28])[C:8]2[O:14][C:13]3[C:15]([Cl:24])=[CH:16][C:17]([NH:19][C:20](=[O:23])[CH2:21][N:30]([CH3:31])[CH3:29])=[CH:18][C:12]=3[CH2:11][S:10](=[O:25])(=[O:26])[C:9]=2[CH:27]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 11430Potassium CarbonateHCID 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 1317285024-Chloro-2-(2-dimethylamino-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

Procedure

A mixture of Example 133 (0.4 g, 0.9 mmol), dimethylamine.HCl (0.44 g, 5.4 mmol) and potassium carbonate (0.75 g, 5.0 mmol) in 10 mL of dry DMF was stirred at 80° C. for 2 h. The reaction mixture was filtered and the solid obtained was washed with water. The filtrate was concentrated, treated with water and extracted with chloroform. The organic layer was washed with water, brine, concentrated and purified using flash chromatography (silica gel, 1% methanol/chloroform) to obtain the title compound. Yield: 0.26 g, (63.73%); 1H NMR (DMSO-d6): δ 1.96 (s, 6H, 2CH3), 2.17 (s, 2H, CH2), 2.3 (s, 3H, CH3), 3.51 (s, 3H, OCH3), 4.45 (s, 2H, CH2), 7.29 (s, 1H, Ar), 7.55 (s, 1H, Ar), 7.67 (s, 1H, Ar), 7.95 (s, 1H, Ar), 9.26 (s, 1H, NH); MS: m/e (EI+) 451 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solid obtained
  3. washwas washed with water
  4. concentrationThe filtrate was concentrated
  5. additiontreated with water
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with water, brine
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-4bdb0be87b9b45cd8705d7b3f853844f
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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