Propylamine → HCID 54340136, compound

HRID 1378226Notes

Reaction equation

HRID 1378226 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]([NH2:29])[CH2:27][CH3:28]>CN(C)C=O>[CH2:26]([NH: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)[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 53721246HCID 53721246, compound

Product 1

HCID 54340136HCID 54340136, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 710 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 0.5 ml (6.0 mmol) of propylamine and stirred at room temperature under argon for 2 hrs. The solution was evaporated, the residue was triturated in 5 ml of water and the crystals were filtered off. Additional crude product was obtained by extracting the aqueous phase with methylene chloride. The combined crude products (0.65 g) were chromatographed on 25 g of silica gel (methylene chloride/methanol 2%, 5%, 10%). There were obtained 540 mg of (S)-1-(5-propylaminomethyl-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 dissolved in 5 ml of acetonitrile and thereupon converted with ethereal hydrochloric acid into the hydrochloride. By recrystallization from acetonitrile there were obtained 560 mg (62%) of (S)-1-(5-propylaminomethyl-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 (1:2) of m.p. 169°-173° (dec.).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated in 5 ml of water
  3. filtrationthe crystals were filtered off
  4. customAdditional crude product was obtained
  5. extractionby extracting the aqueous phase with methylene chloride
  6. customwere chromatographed on 25 g of silica gel (methylene chloride/methanol 2%, 5%, 10%)

Sources & evidence

ORD record
ord-12d38c75a8404fdea4f0b1a27a071dca
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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