Sodium hydride → 5,11-dihydro-11-ethyl-2-methoxy-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2380247Notes

Reaction equation

HRID 2380247 reaction equation
[H-].[Na+].Br[C:4]1[C:9]([NH:10][C:11]([C:13]2[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[C:8]([CH3:22])[CH:7]=[C:6]([O:23][CH3:24])[N:5]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:20]([N:19]1[C:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:11](=[O:12])[NH:10][C:9]2[C:8]([CH3:22])=[CH:7][C:6]([O:23][CH3:24])=[N:5][C:4]1=2)[CH3:21]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 19960032N-(2-Bromo-6-methoxy-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide

Product 1

HCID 152212525,11-dihydro-11-ethyl-2-methoxy-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 47.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.14 g of a 50% dispersion in mineral oil) was added to a solution of N-(2-bromo- 6-methoxy-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide (0.54 g) in pyridine (4 ml), and the resulting mixture was refluxed for 1.5 hours. The cooled mixture was diluted with ethyl acetate, washed with water, and the organic phase was dried (anhydrous magnesium sulfate) and concentrated. The residue was washed with diisopropyl ether and hot ethyl acetate, and then crystallized from ethanol to provide 0.2 g of 5,11-dihydro-11-ethyl-2-methoxy-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one m.p. 249°-251° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 1.5 hours
  2. washwashed with water
  3. dry with materialthe organic phase was dried (anhydrous magnesium sulfate)
  4. concentrationconcentrated
  5. washThe residue was washed with diisopropyl ether and hot ethyl acetate
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-dc2d6d466d6840ce9a7ab52ddb87b348
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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