Diisopropylamine → HCID 22914338, compound

HRID 1378220Notes

Reaction equation

HRID 1378220 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21]Cl)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:25].[CH:26]([NH:29][CH:30]([CH3:32])[CH3:31])([CH3:28])[CH3:27]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:29]([CH:30]([CH3:32])[CH3:31])[CH:26]([CH3:28])[CH3:27])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:25]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 229143657-chloro-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

Product 1

HCID 22914338HCID 22914338, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.20 g (3.14 mmol) of 7-chloro-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 20 ml of N,N-dimethylformamide was treated with 1.59 g (0.0166 mol) of diisopropylamine. After stirring at 80° for 20 hrs. the solution obtained was completely freed from the solvents. The residue was chromatographed over silica gel with methylene chloride/methanol 39:1 as the eluent. The product was recrystallized from ether/n-hexane. There was obtained 0.84 g (60%) of 7-chloro-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 whitish crystals; m.p. 153°-156°.

Workup

  1. customthe solution obtained
  2. customThe residue was chromatographed over silica gel with methylene chloride/methanol 39:1 as the eluent
  3. customThe product was recrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-cc4de12a6118454c9d95b3fa6ab8a005
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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