Diisopropylamine → HCID 21842223, compound

HRID 1737330Notes

Reaction equation

HRID 1737330 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([C:31]1N=C[N:34]2[C:40]3[CH:41]=CC(F)=C[C:39]=3C(=O)N(C)[CH2:36][C:35]=12)=O)C#C.IN1C(=O)CCC1=O.C(NC(C)C)(C)C>C(O)(=O)C.C1COCC1>[CH:35]([N:34]([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)[CH:40]([CH3:41])[CH3:39])([CH3:36])[CH3:31]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 120273N-IodosuccinimideHCID 21842258HCID 21842258, compoundHCID 54122806HCID 54122806, compound

Product 1

HCID 21842223HCID 21842223, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 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 in 300 ml of acetic acid, subsequently completely freed from the solvents, dried azeotropically several times with toluene and dissolved in 500 ml of THF) were treated with 15.4 ml (0.109 mol) of diisopropylamine and stirred at room temperature for 42 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 and the brownish product was chromatographed over silica gel with dichloromethane/methanol 39:1 as the eluent. There was obtained 0.83 g (16%) of 3-(5-diisopropylaminomethyl-oxazol-2-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as yellowish crystals; m.p. 176-178°.

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 brownish product was chromatographed over silica gel with dichloromethane/methanol 39:1 as the eluent

Sources & evidence

ORD record
ord-918d91828ec340cd935548957c836f60
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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