Propylamine → HCID 22914379, compound

HRID 1378224Notes

Reaction equation

HRID 1378224 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].Cl[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([F:26])[C:20]=4[C:19](=[O:27])[N:18]([CH3:28])[CH2:17][C:16]=23)[N:8]=1>CN(C)C=O>[CH2:1]([NH:4][CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([F:26])[C:20]=4[C:19](=[O:27])[N:18]([CH3:28])[CH2:17][C:16]=23)[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 22914357HCID 22914357, compound

Product 1

HCID 22914379HCID 22914379, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 ml (12.2 mmol) of propylamine was added to a suspension of 1.7 g (4.9 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-5-methyl-5,6-dihydro-4H-imidazo-[1,5-a][1,4]benzodiazepin-6-one in 40 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 12 hours. The solution was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous solution was extracted with methylene chloride and the organic phases were dried with magnesium sulfate, filtered and evaporated. The residue was chromatographed (silica gel, ethyl acetate/methanol 9:1). There were obtained 1.21 g (67%) of 3-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, Rf=0.22 (silica gel, ethyl acetate/methanol 4:1).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. dry with materialthe organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed (silica gel, ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-902814d0f7f04ca98ec95c04710c31d8
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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