Diethylamine → HCID 21842266, compound
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[O:16][C:17]([CH2:20]I)=[CH:18][N:19]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>>[CH2:25]([N:27]([CH2:20][C:17]1[O:16][C:15]([C:14]2[N:13]=[CH:12][N:11]3[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:24][C:6]=4[C:7](=[O:23])[N:8]([CH3:22])[CH2:9][C:10]=23)=[N:19][CH:18]=1)[CH2:28][CH3:29])[CH3:26]Participants
Procedure
125 ml of this crude solution of 8-fluoro-3-(5-iodomethyl-oxazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were treated with 11.3 ml (0.109 mol) of diethylamine and stirred at room temperature for 20 hrs. The suspension obtained was completely freed from the solvents, the residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid and extracted. The aqueous-acidic phase was made basic and extracted with ethyl acetate. The organic phase was concentrated, the orange-brownish product was chromatographed over silica gel with ethyl acetate/methanol 17:3 as the eluent and recrystallized from hot ethyl acetate. There was obtained 0.75 g (16%) of 3-(5-diethylaminomethyloxazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as light beige crystals; m.p. 182°-184°. A further 0.39 g of yellowish crystals was obtained from the mother liquor.
Workup
- customThe suspension obtained
- customthe residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid
- extractionextracted
- extractionextracted with ethyl acetate
- concentrationThe organic phase was concentrated
- customthe orange-brownish product was chromatographed over silica gel with ethyl acetate/methanol 17:3 as the eluent
- customrecrystallized from hot ethyl acetate
Sources & evidence
- ORD record
- ord-5ba5950f47254d1bb692273af9912e0a
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05885986
Reaction notes
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