Nevirapine → 11-Cyclopropyl-2,3-dichloro-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 53558

Reaction equation

HRID 53558 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[C:16](C)=[CH:17][CH:18]=[N:19][C:5]2=3)[CH2:3][CH2:2]1.[Cl:21]N1C(=O)CCC1=O.[C:29]([Cl:33])(Cl)(Cl)Cl>>[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[C:16]([CH3:17])=[C:29]([Cl:33])[C:18]([Cl:21])=[N:19][C:5]2=3)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 4463NevirapineHCID 5943Carbon TetrachlorideHCID 31398Chlorosuccinimide2×

Product 1

HCID 1996005311-Cyclopropyl-2,3-dichloro-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Procedure

A mixture of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.5 g) and N-chlorosuccinimide (0.5 g) in carbon tetrachloride (50 mL) was heated under reflux for 6 hours. An additional 0.25 g of N-chlorosuccinimide was added and heating under reflux was continued for 4 hrs more. The mixture was filtered and the solvent was evaporated. The residue was fractionated over silica gel with ethyl acetate/hexane to give the title compound which crystallized from ethyl acetate/ethanol, m.p.>290° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. filtrationThe mixture was filtered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d57e4ca2cc69482f9f8ca5ef95270913
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Linked notes

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