Dipropylamine → HCID 18392572, compound

HRID 1737319Notes

Reaction equation

HRID 1737319 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=3[C:14](=[O:22])[N:13]3[CH2:23][CH2:24][C@H:12]3[C:11]=12)=[O:6])[C:2]#[CH:3].IN1C(=O)CCC1=O.[CH2:33]([NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH3:35]>C(O)(=O)C>[Cl:21][C:20]1[C:15]2[C:14](=[O:22])[N:13]3[CH2:23][CH2:24][C@H:12]3[C:11]3[N:10]([CH:9]=[N:8][C:7]=3[C:5]3[O:6][C:2]([CH2:3][N:36]([CH2:37][CH2:38][CH3:39])[CH2:33][CH2:34][CH3:35])=[CH:1][N:4]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 120273N-IodosuccinimideHCID 86753941HCID 86753941, compound

Product 1

HCID 18392572HCID 18392572, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.30 g (0.0098 mol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid prop-2-ynylamide in 60 ml of acetic acid was treated with 3.30 g (0.0147 mol) of N-iodosuccinimide while gassing with argon. After stirring at room temperature for 24 hrs. the dark brown suspension obtained was completely freed from the solvents and dried azeotropically several times with toluene. The dark viscous residue was dissolved in 60 ml of THF, treated with 11.9 ml (0.0865 mol) of dipropylamine and stirred at room temperature for 24 hrs. The suspension obtained was filtered and the solution was completely freed from the solvents, the residue was partitioned between ethyl acetate and dilute aqueous hydrochloric acid and extracted. The aqueous-acidic phase was made basic and extracted with ethyl acetate. The organic phase was concentrated and the residue was chromatographed over silica gel with dichloromethane/methanol 98:2 as the eluent. There were obtained 1.19 g (28%) of (S)-8-chloro-1-(5-dipropylaminomethyl-oxazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as yellow crystals; m.p. 148-151° (dec.) and [α]D20 =-101.7° (MeOH, c=1%).

Workup

  1. customthe dark brown suspension obtained
  2. dry with materialdried azeotropically several times with toluene
  3. dissolutionThe dark viscous residue was dissolved in 60 ml of THF
  4. stirringstirred at room temperature for 24 hrs
  5. customThe suspension obtained
  6. filtrationwas filtered
  7. customthe residue was partitioned between ethyl acetate and dilute aqueous hydrochloric acid
  8. extractionextracted
  9. extractionextracted with ethyl acetate
  10. concentrationThe organic phase was concentrated
  11. customthe residue was chromatographed over silica gel with dichloromethane/methanol 98:2 as the eluent

Sources & evidence

ORD record
ord-e3ebeaae803f4c06ad667dbbfa34c9f2
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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