Dipropylamine → HCID 22914353, compound

HRID 1378089Notes

Reaction equation

HRID 1378089 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[O:17][C:18]([CH2:21]Cl)=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:25].[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28]>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[O:17][C:18]([CH2:21][N:29]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH3:28])=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:25]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 22914254HCID 22914254, compound

Product 1

HCID 22914353HCID 22914353, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.193 g (0.51 mmol) of 7-chloro-3-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 2 ml of N,N-dimethylformamide was treated with 0.26 g (2.55 mmol) of dipropylamine. After stirring at room temperature for 17 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 at 0°. There were obtained 0.094 g (41%) of 7-chloro-3-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 128°-130°.

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 at 0°

Sources & evidence

ORD record
ord-485e945eb4604249a47c5ac51aa35515
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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