4-Methylmorpholine → 4,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamide

HRID 576299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576299
[Br:1][C:2]1[C:10]([C:11](O)=[O:12])=[CH:9][C:8]([Br:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.[CH3:44][NH:45][O:46][CH3:47]>C(Cl)Cl>[Br:1][C:2]1[C:10]([C:11]([N:45]([O:46][CH3:47])[CH3:44])=[O:12])=[CH:9][C:8]([Br:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 710783864,7-dibromo-2,3-dihydro-1H-indene-5-carboxylic acid

Produkt 1

HCID 867140174,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamideAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of acid 4 (4.8 g, 15.0 mmol) in CH2Cl2 (80 mL) were added EDCI (3.83 g, 20 mmol), HOBT (2.70 g, 20 mmol), NMM (8.8 mL, 80 mmol) and N,O-dimethylhydroxylamine-HCl (1.95 g, 20 mmol) at rt. The mixture was stirred at rt overnight. The reaction mixture was quenched with water (50 mL) and extracted with DCM (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 9 (0.27 g, 0.73 mmol, 7%).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with DCM (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-673e9a4fd0ab442889efe5f5ffddfddf
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034921B2

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