Dimethylformamide → HCID 13344910, compound

HRID 1462180Notes

Reaction equation

HRID 1462180 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]([CH3:22])[CH2:18][CH2:17]1)=S.CN(C)C=O.[C:28](=[O:31])([O-:30])[O-].[K+].[K+].N#CBr.[C:37]([O:40]CC)(=[O:39])[CH3:38]>CCOCC>[C:37]([OH:40])(=[O:39])/[CH:38]=[CH:2]\[C:28]([OH:30])=[O:31].[CH3:22][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

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 204033081-[2-(2-Imidazolylmethyl) phenylthiocarbamoyl]-4-methylpiperazine

Product 1

HCID 13344910HCID 13344910, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 315 mg of 1-[2-(2-imidazolylmethyl)phenylthiocarbamoyl]-4-methylpiperazine, 3.3 ml of dimethylformamide, 276 mg of potassium carbonate, 116 mg of cyanogen bromide and 50 mg of 8-crown-6 ether is stirred at room temperature under nitrogen for 3 hours. It is diluted with ethyl acetate, washed with saturated aqueous sodium chloride, dried and evaporated. The residue is dissolved in acetone, the solution treated with 116 mg of maleic acid and diluted with diethyl ether, to yield 5-(4-methyl-1-piperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine monomaleate of example 1.

Workup

  1. washwashed with saturated aqueous sodium chloride
  2. customdried
  3. customevaporated
  4. dissolutionThe residue is dissolved in acetone
  5. additionthe solution treated with 116 mg of maleic acid
  6. additiondiluted with diethyl ether

Sources & evidence

ORD record
ord-48f0cb4f2522407089775c9ff1e4727a
Source dataset
uspto-grants-1984_07
Patent number
US04459232

Reaction notes

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