Cyanogen Bromide → 5-(4-ethoxycarbonyl-1-piperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine

HRID 1462332Notes

Reaction equation

HRID 1462332 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]1)=S.C(=O)([O-])[O-].[K+].[K+].N#CBr>C(#N)C>[CH2:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][N:16]([C:14]2[N:3]3[CH:4]=[CH:5][N:1]=[C:2]3[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:13]=2)[CH2:17][CH2:18]1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 204033221-[2-(2-Imidazolylmethyl)-phenylthiocarbamoyl]-4-ethoxycarbonylpiperazine

Product 1

HCID 133449165-(4-ethoxycarbonyl-1-piperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 8.9 g of 1-[2-(2-imidazolylmethyl)phenylthiocarbamoyl]-4-ethoxycarbonylpiperazine in 70 ml of acetonitrile, cooled to 0°, was added 2.4 g of solid potassium carbonate while stirring, followed by dropwise addition of a solution of 2.5 g of cyanogen bromide in 10 ml of acetonitrile; the mixture was allowed to warm up to room temperature overnight. The solids were filtered off, washed with ethyl acetate, and the filtrate was evaporated to dryness. The residue was dissolved in methylene chloride, the solution was washed with water, dried over MgSO4, decolorized with charcoal and evaporated to dryness. The residue was chromatographed with 250 g of silica gel using ethyl acetate-methanol (9:1) as eluant to give 5-(4-ethoxycarbonyl-1-piperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine, m.p. 137°-139°.

Workup

  1. filtrationThe solids were filtered off
  2. washwashed with ethyl acetate
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washthe solution was washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was chromatographed with 250 g of silica gel

Sources & evidence

ORD record
ord-c429c66ffaf74b2f90efdf3224229085
Source dataset
uspto-grants-1984_07
Patent number
US04460508

Reaction notes

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