Propylamine → HCID 53831568, compound

HRID 1378241Notes

Reaction equation

HRID 1378241 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[C@@H:9]3[CH2:22][CH2:23][N:8]3[C:7](=[O:24])[C:6]=2[CH:25]=1.[CH2:26]([NH2:29])[CH2:27][CH3:28]>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:29][CH2:26][CH2:27][CH3:28])[O:17][N:16]=4)=[C:10]3[C@@H:9]3[CH2:22][CH2:23][N:8]3[C:7](=[O:24])[C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 54055923HCID 54055923, compound

Product 1

HCID 53831568HCID 53831568, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.13 g (3.0 mmol) of (S)-7-chloro-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 15 ml of N,N-dimethylformamide was treated with 0.74 ml (9.0 mmol) of propylamine and stirred at room temperature under argon for 3 hrs. The solution was evaporated, the residue was taken up in 20 ml of water and the aqueous phase was extracted with methylene chloride. The combined extracts were washed twice with water, dried with sodium sulfate, filtered and evaporated. The crude product was chromatographed on 30 g of silica gel (methylene chloride/acetone 4:1, then 2:1 and finally methylene chloride/methanol 9:1). There were obtained 840 mg of (S)-7-chloro-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 in acetonitrile in the presence of fumaric acid into the fumarate. By recrystallization from acetonitrile there were obtained 588 mg (35%) of (S)-7-chloro-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 fumarate (1:1.4) of m.p. 135°-140° (dec.).

Workup

  1. customThe solution was evaporated
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. washThe combined extracts were washed twice with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on 30 g of silica gel (methylene chloride/acetone 4:1

Sources & evidence

ORD record
ord-4ccab182e7154ca1b2a9b93003a3a2fb
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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