Water → 13-bromo-5-chloro-2-ethyl-9-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

HRID 2229308Notes

Reaction equation

HRID 2229308 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:22]=[N:21][C:7]2[N:8]([CH2:19][CH3:20])[C:9]3[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=3[NH:11][C:12](=[O:13])[C:6]=2[CH:5]=1.O.[CH3:24]N(C=O)C>>[Br:3][C:4]1[CH:22]=[N:21][C:7]2[N:8]([CH2:19][CH3:20])[C:9]3[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=3[N:11]([CH3:24])[C:12](=[O:13])[C:6]=2[CH:5]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10498284HCID 10498284, compound

Product 1

HCID 1059515213-bromo-5-chloro-2-ethyl-9-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-oneYield 94%

Conditions

Temperature
50 °C

Procedure

Solid NaH (60% oil dispersion, 3.46 g, 86.1 mmol) was added over 30 min to a solution of 8-bromo-2-chloro-5,11-dihydro-11-ethyl-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (23.4 g, 66.3 mmol) in DMF (220 mL) at 50° C. The mixture was stirred at 50° C. for 1 h then was allow to cool to room temperature. The mixture was poured into water (1 L) and the resulting suspension was filtered. The solid was successively washed with water and hexane then dried under reduced pressure to give the title compound (23.0 g, 94% yield).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting suspension was filtered
  3. washThe solid was successively washed with water and hexane
  4. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-8d49f94fbe994533b5dacb60c25330bd
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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