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

HRID 1172485Notes

Reaction equation

HRID 1172485 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:29])[C:10]2[O:16][C:15]3[C:17]([Cl:25])=[CH:18][C:19]([NH:21][CH2:22][CH2:23]Cl)=[CH:20][C:14]=3[CH2:13][S:12](=[O:27])(=[O:26])[C:11]=2[CH:28]=1)=[O:6]>CO>[CH3:3][O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:29])[C:10]2[O:16][C:15]3[C:17]([Cl:25])=[CH:18][C:19]([NH:21][CH2:22][CH2:23][NH:2][CH3:1])=[CH:20][C:14]=3[CH2:13][S:12](=[O:27])(=[O:26])[C:11]=2[CH:28]=1)=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 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 1317284564-Chloro-6-methyl-2-(2-methylamino-ethylamino)-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 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 30% methanolic methylamine solution (4 mL) was added to a solution of the carboxylic acid of Example 56k (0.5 g, 1.16 mmol) in methanol, in a pressure reactor vessel under nitrogen atmosphere and kept at 110° C. for 4 h. The reaction mixture was cooled, concentrated partially and the solid that precipitated was filtered, washed with methanol, dried, treated with methanolic HCl solution (10 mL) and stirred at 70° C. for 1.5 h. The reaction mixture was cooled and the solid that precipitated was filtered and washed with methanol to obtain the title compound as an off white solid. Yield: 0.325 g, (65.92%); 1H NMR (DMSO-d6): δ 2.50 (d, 3H, CH3), 2.80 (s, 3H, CH3), 3.10 (t, 2H, CH2), 3.30 (t, 2H, CH2), 3.90 (s, 3H, OCH3), 5.10 (s, 2H, CH2), 6.85-6.90 (m, 2H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 1H, Ar), 9.0 (t, 1H, NH); MS: m/e (ES+) 425 (M+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated partially
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with methanol
  6. customdried
  7. additiontreated with methanolic HCl solution (10 mL)
  8. temperatureThe reaction mixture was cooled
  9. customthe solid that precipitated
  10. filtrationwas filtered
  11. washwashed with methanol

Sources & evidence

ORD record
ord-3b2d81b49cf34fe6a4bf628f8fc245a6
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

Loading…