Methylamine → 8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14](C4ON=C(CN5C(=O)C6=CC=CC=C6C5=O)N=4)=[C:10]3[CH2:9][N:8]([CH3:32])[C:7](=[O:33])[C:6]=2[CH:34]=1.CN>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][CH:14]=[C:10]3[CH2:9][N:8]([CH3:32])[C:7](=[O:33])[C:6]=2[CH:34]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
10.1 g (22 mmol) of 8-fluoro-5,6-dihydro-5-methyl-3-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were heated to 65° in 220 ml of ethanol, whereupon 150 ml of 33% ethanolic methylamine solution were added dropwise within 100 min. After completion of the addition the solution was heated for a further 17 hrs. and then cooled in an ice bath, whereby white crystals separated. These were filtered off and dried in a vacuum. After recrystallization from ethanol there were obtained 3.05 g of 3-(3-aminomethyl)-1,2,4-oxadiazol-5-yl) -8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 208°-217°. A further 2.5 g of product were obtained by chromatography on silica gel with methylene chloride/methanol 19:1, then 9:1. Total yield: 5.55 g (77%).
Workup
- additionwere added dropwise within 100 min
- additionAfter completion of the addition the solution
- temperaturewas heated for a further 17 hrs
- temperatureand then cooled in an ice bath
- customwhereby white crystals separated
- filtrationThese were filtered off
- customdried in a vacuum
- customAfter recrystallization from ethanol
Sources & evidence
- ORD record
- ord-45e30136b6a34627b07e54ae9eb9596e
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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