11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one → 5,11-Dihydro-11-[[7-methyl-3,7-diazabicyclo[3.3.0]-oct-3-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 1646189Notes

Reaction equation

HRID 1646189 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[CH3:20][N:21]1[CH2:28][CH:27]2[CH:23]([CH2:24][NH:25][CH2:26]2)[CH2:22]1>CN(C)C=O>[CH3:20][N:21]1[CH2:28][CH:27]2[CH:23]([CH2:24][N:25]([C:2]([N:4]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[C:8](=[O:15])[NH:7][C:6]4[CH:16]=[CH:17][CH:18]=[N:19][C:5]3=4)=[O:3])[CH2:26]2)[CH2:22]1

Participants

4

Reactant 2

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 129585332-Methyloctahydropyrrolo(3,4-c)pyrrole

Product 1

HCID 151069055,11-Dihydro-11-[[7-methyl-3,7-diazabicyclo[3.3.0]-oct-3-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.9 g (18 mmoles) of 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2.3 g of 3- methyl-3,7-diazabicyclo[3.3.0]octane in 75 ml of dry dimethylformamide was stirred for 20 hours at ambient temperature. The reaction mixture was concentrated in vacuo, the residue was divided between 1N hydrochloric acid and methylene chloride. The organic phase was washed two further times using 1N hydrochloric acid and once using water. The combined aqueous phases were rendered basic using potassium carbonate and extracted using methylene chloride (3×150 ml). The combined methylene chloride phases were dried over magnesium sulphate, concentrated and the crude material was recrystallised from acetonitrile. 2.9 g (41% of theory) of colourless crystals of m.p. 157°-159° C. were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe organic phase was washed two further times
  3. extractionextracted
  4. dry with materialThe combined methylene chloride phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customthe crude material was recrystallised from acetonitrile
  7. custom2.9 g (41% of theory) of colourless crystals of m.p. 157°-159° C. were obtained

Sources & evidence

ORD record
ord-5d97f6f3e2434325a97cd35d393045a6
Source dataset
uspto-grants-1993_01
Patent number
US05179090

Reaction notes

Loading…