Dipropylamine → HCID 53770728, compound

HRID 1378092Notes

Reaction equation

HRID 1378092 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:18]([CH2:21]Cl)=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:18]([CH2:21][N:29]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH3:28])=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 53864688HCID 53864688, compound

Product 1

HCID 53770728HCID 53770728, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.88 g (5 mmol) of (S)-8-chloro-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred at room temperature over the weekend with 1.12 g (11 mmol) of dipropylamine and 10 ml of N,N-dimethylformamide. After evaporating the reaction mixture the residue was dissolved in methylene chloride and the solution was washed twice with water and dried over magnesium sulfate. After evaporating the solvent and crystallizing the residue from ethyl acetate and hexane there were obtained 2.15 g (98%) of (S)-8-chloro-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 134°-136°, which was converted into the hydrochloride of melting point 235°-237°.

Workup

  1. customAfter evaporating the reaction mixture the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customcrystallizing the residue from ethyl acetate

Sources & evidence

ORD record
ord-50cf7a1960234ab48b978d65daae2fd2
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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