Propylamine → HCID 22914517, compound

HRID 1378235Notes

Reaction equation

HRID 1378235 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20]Cl)[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1.[CH2:25]([NH2:28])[CH2:26][CH3:27]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20][NH:28][CH2:25][CH2:26][CH3:27])[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 22914400HCID 22914400, compound

Product 1

HCID 22914517HCID 22914517, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 mg (0.54 mmol) of 8-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 4 ml of N,N-dimethylformamide was treated with 0.136 ml (1.65 mmol) of propylamine and stirred at room temperature under argon for 1.5 hrs. The solution was evaporated and the residue was triturated in 10 ml of water. The aqueous phase was extracted with methylene chloride and the combined extracts were washed twice with water, dried with sodium sulfate, filtered and evaporated. The combined crude products were chromatographed on 30 g of silica gel (ethyl acetate methylene chloride/methanol 9:1). There were obtained 126 mg of 8-chloro-3-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as a foam which was converted in acetonitrile with ethereal hydrochloric acid into the hydrochloride. By crystallization from hot acetonitrile there were obtained 102 mg (42%) of 8-chloro-1-(5-propylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1.8) of m.p. 230°-240° (dec.).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated in 10 ml of water
  3. extractionThe aqueous phase was extracted with methylene chloride
  4. washthe combined extracts were washed twice with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customwere chromatographed on 30 g of silica gel (ethyl acetate methylene chloride/methanol 9:1)

Sources & evidence

ORD record
ord-41660ce4b3924af9ab2161ca439b85ef
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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