Diethylamine → HCID 22914460, compound

HRID 1378068Notes

Reaction equation

HRID 1378068 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.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>CN(C)C=O>[CH2:25]([N:27]([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)[CH2:28][CH3:29])[CH3:26]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914460HCID 22914460, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.5 g (0.0043 mol) 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 15 ml of dimethylformamide was treated with 1.6 g (0.022 mol) of diethylamine. After stirring at room temperature for 16 hrs. the solution obtained was freed completely from the solvents. The residue was chromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent. There were obtained 1.33 g (81%) of 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. 172°-174°.

Workup

  1. customthe solution obtained
  2. customThe residue was chromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent

Sources & evidence

ORD record
ord-125639d20de4475cb5b5188be17dd061
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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