Dimethylformamide → 3-[3-(bis-cyclopropylmethylaminomethyl)-1,2,4-oxadiazol-5-yl]-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378066Notes

Reaction equation

HRID 1378066 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([CH:30]([CH3:32])[CH3:31])C(C)C)C.Br[CH2:34][CH:35]1[CH2:37][CH2:36]1.[CH3:38]N(C)C=O>>[CH:37]1([CH2:36][N:1]([CH2:2][C:3]2[N:7]=[C:6]([C:8]3[N:9]=[CH:10][N:11]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=34)[O:5][N:4]=2)[CH2:38][CH:30]2[CH2:32][CH2:31]2)[CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 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 700755963-[3-(bis-cyclopropylmethylaminomethyl)-1,2,4-oxadiazol-5-yl]-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 48%

Procedure

2 g (6.44 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, 20 ml of N,N-dimethylformamide, 3.8 ml (22.5 mmol) of N-ethyldiisopropylamine and 1.6 ml (14.8 mmol) of bromomethylcyclopropane were stirred at 80° for 4 hours. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was washed with water, dried and concentrated. By chromatography on 220 g of silica gel while eluting with methylene chloride/ethyl acetate 1/1 there were obtained 1.3 g (48%) of 3-[3-(bis-cyclopropylmethylaminomethyl)-1,2,4-oxadiazol-5-yl ]-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 170°-174°.

Workup

  1. customAfter evaporating the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. washBy chromatography on 220 g of silica gel while eluting with methylene chloride/ethyl acetate 1/1 there

Sources & evidence

ORD record
ord-e90aaf0c78804ff499dd921af6c74ec8
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…