Hydrochloric Acid → HCID 59335136, compound

HRID 1517957Notes

Reaction equation

HRID 1517957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22](O)=[O:23])=[CH:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:25](N1C=CN=C1)([N:27]1C=CN=[CH:28]1)=O.CNC.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:25][N:27]([CH3:28])[C:22]([C:17]1[NH:18][C:19]2[C:15]([CH:16]=1)=[CH:14][C:13]([NH:12][S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:10])=[O:11])=[CH:21][CH:20]=2)=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59335126HCID 59335126, compound

Product 1

HCID 59335136HCID 59335136, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

55 mg 5-(3,5-dichloro-phenylsulphonylamino)-1H-indole-2-carboxylic acid are dissolved in 2 ml of tetrahydrofuran, combined with 25 mg carbonyldiimidazole, stirred for 3 hours at ambient temperature and for 1 hour at 40° C. Then the mixture is combined with 300 μl dimethylamine (2 M in tetrahydrofuran) and stirred overnight. The solvent is eliminated in vacuo and the residue is divided between ethyl acetate and 0.5 N hydrochloric acid. The organic phase is washed with water and saturated sodium chloride solution and dried on magnesium sulphate. After elimination of the solvents in vacuo the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10 to 30:70).

Workup

  1. stirringstirred overnight
  2. washThe organic phase is washed with water and saturated sodium chloride solution
  3. customdried on magnesium sulphate
  4. customAfter elimination of the solvents in vacuo the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10 to 30:70)

Sources & evidence

ORD record
ord-95d977bc9f574dea84b5ac605522ecf6
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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