Cyclopropylamine → HCID 22914557, compound

HRID 1378133Notes

Reaction equation

HRID 1378133 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][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CN(C)C=O>[CH:25]1([NH:28][CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]3[N:9]=[CH:10][N:11]4[C:17]5[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=5[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=34)[N:4]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914557HCID 22914557, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.7 g (5 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at room temperature for 2 hours with 5 ml (7.2 mmol) of cyclopropylamine and 15 ml of N,N-dimethylformamide. After evaporation of the reaction mixture the residue was taken up in methylene chloride and washed with aqueous ammonia. After drying the organic phase over magnesium sulfate, evaporation of the solvent and recrystallization of the residue from ethyl acetate and hexane there were obtained 1.17 g (65%) of 3-(5-cyclopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 176°-178°, which was converted into the hydrochloride.

Workup

  1. customAfter evaporation of the reaction mixture the residue
  2. washwashed with aqueous ammonia
  3. customAfter drying the organic phase
  4. customover magnesium sulfate, evaporation of the solvent and recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-446f6c0d77224ce7a65ce99e293ad35b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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