Diisopropylamine → HCID 22914262, compound

HRID 1378242Notes

Reaction equation

HRID 1378242 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1.[CH:25]([NH:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>CN(C)C=O>[CH:25]([N:28]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1)[CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914262HCID 22914262, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.04 g (3.0 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]-[1,4]benzodiazepin-6-one in 10 ml of N,N-dimethylformamide was treated with 1.27 ml (9.0 mmol) of diisopropylamine. After stirring at room temperature for 18 hrs. the solution obtained was concentrated and the residue was taken up in 10 ml of water and stirred in an ultrasound bath for 2 hrs. The crystals were filtered off under suction and dissolved in methylene chloride, and the solution was dried with sodium sulfate, is filtered and evaporated. The crude material was chromatographed on silica gel (ethyl acetate), dissolved in acetonitrile and acidified with ethereal hydrochloric acid. The solution was again evaporated and the residue was recrystallized from acetonitrile. After drying in a vacuum there were obtained 542 mg (38%) of 3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals of m.p. 173°-178° (dec.).

Workup

  1. customthe solution obtained
  2. concentrationwas concentrated
  3. stirringstirred in an ultrasound bath for 2 hrs
  4. filtrationThe crystals were filtered off under suction
  5. dissolutiondissolved in methylene chloride
  6. dry with materialthe solution was dried with sodium sulfate
  7. filtrationis filtered
  8. customevaporated
  9. customThe crude material was chromatographed on silica gel (ethyl acetate)
  10. dissolutiondissolved in acetonitrile
  11. customThe solution was again evaporated
  12. customthe residue was recrystallized from acetonitrile
  13. customAfter drying in a vacuum there

Sources & evidence

ORD record
ord-e8d2bd18a9b5428287a9eb3587e41925
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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