Dimethylformamide → HCID 13344910, compound

HRID 2164817Notes

Reaction equation

HRID 2164817 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-656aa81d79b34c16a903d02fb56d6c78
Source dataset
uspto-grants-1985_03
Patent number
US04507311

Reaction notes

Loading…