Ethylamine → HCID 22914450, compound

HRID 1378208Notes

Reaction equation

HRID 1378208 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]([NH2:27])[CH3:26]>CN(C)C=O.CCOCC>[CH2:25]([NH: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)[CH3:26]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914450HCID 22914450, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

0.66 g (1.9 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 was dissolved in 20 ml of N,N-dimethylformamide. A weak stream of ethylamine gas was introduced at room temperature, the reaction temperature rising to 36°. 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 19:1 as the eluent. After concentration there was obtained a beige foam which was taken up in ether. There was obtained 0.40 g (59%) of 3-(5-ethylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as beige crystals; m.p. 166°-168°.

Workup

  1. customrising to 36°
  2. customthe solution obtained
  3. customThe residue was chromatographed over silica gel with methylene chloride/methanol 19:1 as the eluent
  4. concentrationAfter concentration
  5. customthere was obtained a beige foam which

Sources & evidence

ORD record
ord-73a796d5c33e4360b82400ecbf0edbf3
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…