o-Bis(bromomethyl)benzene → 5,6-dihydro-3-(3-isoindolin-2-ylmethyl-1,2,4-oxadiazol-5-yl)-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378054Notes

Reaction equation

HRID 1378054 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[O:5][N:4]=1.C(N(C(C)C)C(C)C)C.Br[CH2:34][C:35]1[C:36]([CH2:41]Br)=[CH:37][CH:38]=[CH:39][CH:40]=1>CN(C)C=O>[CH2:41]1[C:36]2[C:35](=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:34][N:1]1[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[O:5][N:4]=1

Participants

5

Reactant 3

HCID 66665o-Bis(bromomethyl)benzeneHCID 81531DiisopropylethylamineHCID 229142163-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 540922635,6-dihydro-3-(3-isoindolin-2-ylmethyl-1,2,4-oxadiazol-5-yl)-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.28 g (4.1 mmol) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 25 ml of N,N-dimethylformamide, 2 ml (11.7 mmol) of N-ethyldiisopropylamine and 1.19 g (4.5 mmol) of α,α'-dibromo-o-xylene were stirred at room temperature for 4 hours. After evaporating the solvent the residue was chromatographed on 180 g of silica gel while eluting with ethyl acetate. The uniform fractions were evaporated. There was obtained 0.39 g (23%) of 5,6-dihydro-3-(3-isoindolin-2-ylmethyl-1,2,4-oxadiazol-5-yl)-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 155°-160°.

Workup

  1. customAfter evaporating the solvent the residue
  2. customwas chromatographed on 180 g of silica gel
  3. washwhile eluting with ethyl acetate
  4. customThe uniform fractions were evaporated

Sources & evidence

ORD record
ord-353acc0fbbe04866b9b6e4fe877b50ca
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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