Sodium hydride → Dipyridodiazepinone deriv. 36

HRID 53526Notes

Reaction equation

HRID 53526 reaction equation
[H-].[Na+].Br[C:4]1[C:9]([N:10]([CH3:22])[C:11]([C:13]2[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:23][CH3:24])[N:5]=1>C1(C)C(C)=CC=CC=1>[CH2:20]([N:19]1[C:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:11](=[O:12])[N:10]([CH3:22])[C:9]2[CH:8]=[CH:7][C:6]([O:23][CH3:24])=[N:5][C:4]1=2)[CH3:21]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 10618812N-(2-Bromo-6-methoxy-3-pyridinyl)-2-ethylamino-N-methyl-3-pyridinecarboxamide

Product 1

HCID 463556Dipyridodiazepinone deriv. 36Yield 47.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Sodium hydride (0.9 g of a 50% dispersion in mineral oil) was added to a solution of N-(2-bromo-6-methoxy-3-pyridinyl)-2-ethylamino-N-methyl-3-pyridinecarboxamide (1.4 g) in xylene (20 ml) and the mixture refluxed for 2 hours. After cooling, the mixture was quenched with methanol, diluted with ethyl acetate, and washed with water. The organic phase was dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (ethyl acetate/hexane, 1:4) to give fairly pure product, which was then recrystallized twice from ethyl acetate/hexane to give 0.52 g of pure 5,11-dihydro-11-ethyl-2-methoxy-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, m.p. 116°-118° C.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe mixture was quenched with methanol
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified on a silica gel column (ethyl acetate/hexane, 1:4)
  9. customto give fairly pure product, which
  10. customwas then recrystallized twice from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d48385fc511b47c786100ed022685bee
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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