Propylamine → (S)-7-fluoro-1-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1378157Notes

Reaction equation

HRID 1378157 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]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1.[CH2:26]([NH2:29])[CH2:27][CH3:28]>CN(C)C=O>[F:22][C:20]1[CH:19]=[CH:18][C:17]2[N:11]3[CH:10]=[N:9][C:8]([C:5]4[N:4]=[C:3]([CH2:2][NH:29][CH2:26][CH2:27][CH3:28])[O:7][N:6]=4)=[C:12]3[C@@H:13]3[CH2:25][CH2:24][N:14]3[C:15](=[O:23])[C:16]=2[CH:21]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 54062820HCID 54062820, compound

Product 1

HCID 53665386(S)-7-fluoro-1-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 g (5 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred at room temperature for 2 hours with 2 g (34 mmol) of propylamine and 20 ml of N,N-dimethylformamide. By evaporation of the solvent and chromatography of the residue on silica gel while eluting with ethyl acetate/methanol 9/1 there were obtained 1.4 g (73%) of (S)-7-fluoro-1-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride (amorphous).

Workup

  1. customBy evaporation of the solvent and chromatography of the residue on silica gel
  2. washwhile eluting with ethyl acetate/methanol 9/1 there

Sources & evidence

ORD record
ord-179df856417941c1b41565ad27e64a9d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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