Dipropylamine → HCID 54359519, compound

HRID 1378225Notes

Reaction equation

HRID 1378225 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][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1.[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28]>CN(C)C=O>[CH2:26]([N:29]([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][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1)[CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 53721246HCID 53721246, compound

Product 1

HCID 54359519HCID 54359519, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 711 mg (2.0 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 10 ml of N,N-dimethylformamide was treated with 0.82 ml (6.0 mmol) of dipropylamine and stirred at room temperature under argon for 2 hrs. The solution was evaporated, the residue was triturated in 10 ml of water and the crystals were filtered off. The crude product was chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1, then 4:1). There were obtained 840 mg of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted with ethereal hydrochloric acid into the hydrochloride. By recrystallization from acetonitrile there were obtained 685 mg (73%) of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride (1:1.3) of m.p. 137°-140° (dec.).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated in 10 ml of water
  3. filtrationthe crystals were filtered off
  4. customThe crude product was chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1

Sources & evidence

ORD record
ord-e6b481cac6124835964dc32b3136d08f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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