Acetone → HCID 54435499, compound

HRID 1953252Notes

Reaction equation

HRID 1953252 reaction equation
Cl.[CH3:2][O:3][C:4]([CH2:6][N:7]([S:28]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[N:39]=[CH:38][CH:37]=[CH:36]2)(=[O:30])=[O:29])[C:8]1[CH:27]=[CH:26][C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[NH:21])=[CH:18][CH:17]=3)=[N:14][C:10]=2[CH:9]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH3:51][O:52][C:53](Cl)=[O:54]>O>[CH3:2][O:3][C:4]([CH2:6][N:7]([S:28]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[N:39]=[CH:38][CH:37]=[CH:36]2)(=[O:29])=[O:30])[C:8]1[CH:27]=[CH:26][C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[N:21][C:53]([O:52][CH3:51])=[O:54])=[CH:18][CH:17]=3)=[N:14][C:10]=2[CH:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 23302504HCID 23302504, compound

Product 1

HCID 54435499HCID 54435499, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.7 g (1.2 mmol) of 4-[(5-(N-methoxycarbonylmethyl-quinolin-8-yl-sulphonylamino)-1-methyl-1H-benzimidazol-2-yl)-methyl]-benzamidine-hydrochloride and 0.66 g (4.8 mmol) of potassium carbonate are dissolved in 5 ml water and 20 ml acetone and after the addition of 0.12 9 (1.3 mmol) of methylchloroformate the mixture is stirred for 30 minutes at ambient temperature. The solvent is evaporated off, the residue chromatographed on silica gel and eluted with methylene chloride/methanol 40:1. The desired fractions are concentrated by evaporation, the residue is triturated with ether and suction filtered.

Workup

  1. customThe solvent is evaporated off
  2. customthe residue chromatographed on silica gel
  3. washeluted with methylene chloride/methanol 40:1
  4. concentrationThe desired fractions are concentrated by evaporation
  5. customthe residue is triturated with ether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-dcc3a77ccce1463daadac34f056412f6
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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