Potassium Carbonate → HCID 67264245, compound

HRID 1687707Notes

Reaction equation

HRID 1687707 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[C:6]2[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([O:16][CH3:17])[C:5]=2[CH2:4][CH2:3]1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[CH2:10]([N:7]1[C:8](=[O:9])[CH:2]([N:1]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:3][CH2:4][C:5]2[C:15]([O:16][CH3:17])=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=[CH:12][C:6]1=2)[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 21521Bis(2-bromoethyl) ether2×HCID 67264474HCID 67264474, compound

Product 1

HCID 67264245HCID 67264245, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 3-Amino-1-ethyl-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (0.8 g), 1-Bromo-2-(2-bromo-ethoxy)-ethane (797 mg) and Potassium carbonate (879 mg) in Acetonitrile (37 mL), heat to 85° C., After 2 days, added another eq of Potassium carbonate and 0.5 eq of 1-Bromo-2-(2-bromo-ethoxy)-ethane and continue heating. Diluted with CH2Cl2, filter, the material was concentrated onto Celite and purified by ISCO chromatography (120 g, SiO2, gradient elution 0% MeOH/DCM/to 110% MeOH/DCM) to give 1-ethyl-6-methoxy-3-morpholin-4-yl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as an orange solid (334 mgs). 1H-NMR (CDCl3): 7.86 (d, J=8.8 Hz, 1H), 7.09 (d, J=8.6 Hz, 1H), 4.32-4.22 (m, 1H), 3.96 (s, 3H), 3.73-3.60 (m, 5H), 3.27-3.23 (m, 1H), 2.97-2.92 (m, 1H), 2.72-2.55 (m, 4H), 2.54-2.45 (m, 1H), 2.39-2.23 (m, 2H), 1.20 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturecontinue heating
  2. filtrationfilter
  3. concentrationthe material was concentrated onto Celite
  4. custompurified by ISCO chromatography (120 g, SiO2, gradient elution 0% MeOH/DCM/to 110% MeOH/DCM)

Sources & evidence

ORD record
ord-8dbb323c320b49a98a043b54d65470fd
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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