Dipropylamine → HCID 21842230, compound

HRID 1418918Notes

Reaction equation

HRID 1418918 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][C:19]([F:22])=[C:20]([Cl:21])[C:15]=3[C:14](=[O:23])[N:13]([CH3:24])[CH2:12][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:23])[N:13]([CH3:24])[CH2:12][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][C:19]=1[F:22]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 120273N-IodosuccinimideHCID 54289847HCID 54289847, compound

Product 1

HCID 21842230HCID 21842230, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.49 g (0.010 mol) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid prop-2-ynylamide in 200 ml of acetic acid was treated with 3.38 g (0.0151 mol) of N-iodosuccinimide while gassing with argon. After stirring at room temperature for 53 hrs. the dark suspension obtained was completely freed from the solvents and dried azeotropically several times with toluene. The red-brown residue was dissolved in 100 ml of THF, treated with 11.9 ml (0.087 mol) of dipropylamine and stirred at room temperature for 16 hrs. The suspension obtained was completely freed from the solvents, the residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid and extracted. The aqueous-acidic phase was made basic and extracted with ethyl acetate. The organic phase was concentrated and the yellow-brown product was chromatographed over basic Alox (grade III) with dichloromethane/ethyl acetate 17:3 as the eluent. There were obtained 1.1 g (25%) of 7-chloro-3-(5-dipropylaminomethyl-oxazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as a yellow foam. A sample was recrystallized from isopropyl ether; m.p. 110°-112°.

Workup

  1. customthe dark suspension obtained
  2. dry with materialdried azeotropically several times with toluene
  3. dissolutionThe red-brown residue was dissolved in 100 ml of THF
  4. stirringstirred at room temperature for 16 hrs
  5. customThe suspension obtained
  6. customthe residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid
  7. extractionextracted
  8. extractionextracted with ethyl acetate
  9. concentrationThe organic phase was concentrated
  10. customthe yellow-brown product was chromatographed over basic Alox (grade III) with dichloromethane/ethyl acetate 17:3 as the eluent

Sources & evidence

ORD record
ord-9ed113f28dd8496181ce6a88a7ca6b23
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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