Piperidine → HCID 21842236, compound

HRID 1737334Notes

Reaction equation

HRID 1737334 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.C(NC(C1N=C[N:34]2[C:40]3[CH:41]=[CH:42][C:43](F)=[CH:44]C=3C(=O)N(C)CC=12)=O)C#C.IN1C(=O)CCC1=O.N1CCCCC1>C1COCC1>[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][N:34]5[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]5)=[CH:18][N:19]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 120273N-IodosuccinimideHCID 21842258HCID 21842258, compoundHCID 54122806HCID 54122806, compound

Product 1

HCID 21842236HCID 21842236, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

125 ml of a crude THF 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 (prepared from 15.6 g (0.050 mol) of 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid prop-2-ynylamide and 16.9 g (0.075 mol) of N-iodosuccinimide, subsequently completely freed from the solvents, dried azeotropically several times with toluene and dissolved in 500 ml of THF) were treated with 10.7 ml (0.109 mol) of piperidine and stirred at room temperature for 3 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 beige-brown product was chromatographed over silica gel with ethyl acetate/methanol 4:1 as the eluent and recrystallized from hot ethyl acetate. There was obtained 0.85 g (17%) of 8-fluoro-5-methyl-3-(5-piperidin-1-ylmethyl-oxazol-2-yl)-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as yellowish crystals; m.p. 191-193°.

Workup

  1. dry with materialdried azeotropically several times with toluene
  2. dissolutiondissolved in 500 ml of THF)
  3. customThe suspension obtained
  4. customthe residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid
  5. extractionextracted
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic phase was concentrated
  8. customthe beige-brown product was chromatographed over silica gel with ethyl acetate/methanol 4:1 as the eluent
  9. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-12fa3262e5d548ce94b5038ee491bece
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

Loading…