Diethylamine → HCID 22914330, compound

HRID 1378214Notes

Reaction equation

HRID 1378214 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].[CH2:26]([NH:28][CH2:29][CH3:30])[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:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:25]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 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 22914330HCID 22914330, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.30 g (3.4 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 13 ml of N,N-dimethylformamide was treated with 1.24 g (0.017 mol) of diethylamine. After stirring at room temperature for 16 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 1.3 g (91%) of 7-chloro-3-(5-diethylaminomethyl-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; m.p. 140°-144° (dec.).

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-559c23befd194258a154471e80fb1ee9
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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