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

HRID 1462443Notes

Reaction equation

HRID 1462443 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-6478a0d867c84e5eb745d0d7bdb2a951
Source dataset
uspto-grants-1984_07
Patent number
US04460587

Reaction notes

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