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

HRID 1172482Notes

Reaction equation

HRID 1172482 reaction equation
[NH3:1].[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]([CH3:28])[C:9]2[O:15][C:14]3[C:16]([Cl:24])=[CH:17][C:18]([NH:20][CH2:21][CH2:22]Cl)=[CH:19][C:13]=3[CH2:12][S:11](=[O:26])(=[O:25])[C:10]=2[CH:27]=1)=[O:5]>CO>[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]([CH3:28])[C:9]2[O:15][C:14]3[C:16]([Cl:24])=[CH:17][C:18]([NH:20][CH2:21][CH2:22][NH2:1])=[CH:19][C:13]=3[CH2:12][S:11](=[O:25])(=[O:26])[C:10]=2[CH:27]=1)=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 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 1317284522-(2-Amino-ethylamino)-4-chloro-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 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Aqueous ammonia solution (2.5 mL, 30%) was added to a solution of Example 56k (0.4 g, 0.93 mmol) in methanol (1 mL). The reaction mixture was sealed under argon in a reactor vessel and kept in an oven at 120° C. for 2 h. It was concentrated and the solid obtained was washed thoroughly with methanol to remove excess ammonia and dried under vacuo. It was treated with a methanolic HCl solution and stirred at 70° C. for 3 h. The reaction mixture was concentrated, treated with 10% aqueous sodium bicarbonate solution and extracted with ethylacetate. The organic layer was washed with water, brine, dried, and purified using flash chromatography (silica gel, 10% methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.340 g, (89.23%); 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.00 (t, 2H, CH2), 3.35 (t, 2H, CH2), 3.90 (s, 3H, OCH3), 5.20 (s, 2H, CH2), 6.40 (t, 1H, NH), 6.80 (s, 2H, Ar), 7.80 (t, 2H, NH2), 8.15 (s, 1H, Ar) and 8.30 (s, 1H, Ar). MS: m/e (CI+) 411 (M+).

Workup

  1. customThe reaction mixture was sealed under argon in a reactor vessel
  2. concentrationIt was concentrated
  3. customthe solid obtained
  4. washwas washed thoroughly with methanol
  5. customto remove excess ammonia
  6. customdried under vacuo
  7. additionIt was treated with a methanolic HCl solution
  8. concentrationThe reaction mixture was concentrated
  9. additiontreated with 10% aqueous sodium bicarbonate solution
  10. extractionextracted with ethylacetate
  11. washThe organic layer was washed with water, brine
  12. customdried
  13. custompurified

Sources & evidence

ORD record
ord-7d6849e433e44558a9f9e96024b088d3
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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