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

HRID 2164813Notes

Reaction equation

HRID 2164813 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°, is 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 is allowed to warm up to room temperature overnight. The solids are filtered off, washed with ethyl acetate, and the filtrate is evaporated to dryness. The residue is dissolved in methylene chloride, the solution is washed with water, dried over MgSO4, decolorized with charcoal and evaporated to dryness. The residue is 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 are filtered off
  2. washwashed with ethyl acetate
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washthe solution is washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue is chromatographed with 250 g of silica gel

Sources & evidence

ORD record
ord-ef36dcf0d3644bb48e3d753b02803dd6
Source dataset
uspto-grants-1985_03
Patent number
US04507311

Reaction notes

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