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

HRID 2206672Notes

Reaction equation

HRID 2206672 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-be4fe7e2000b4bdb9a5a8ed9d181d2b3
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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