HCID 22118506, compound → HCID 178523903, compound

HRID 365287Notes

Reaction equation

HRID 365287 reaction equation
[C:1]([NH:9][C:10](=[N:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1)SC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:36]1[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][NH2:44])[N:38]=[CH:37]1>N1C=CC=CC=1>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:17]([CH2:16][CH2:15][CH2:14][NH:13][C:10]([NH:44][CH2:43][CH2:42][CH2:41][C:39]2[N:38]=[CH:37][NH:36][CH:40]=2)=[N:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 22118506HCID 22118506, compoundHCID 178510931HCID 178510931, compound

Product 1

HCID 178523903HCID 178523903, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the above isothiourea (5.0 g, 9.133 mmol) in dry pyridine (70 ml) was added 3-(1H-imidazol-4-yl)propyl amine (1.26 g, 10.05 mmol) and the resulting mixture was stirred at reflux temperature for 10 h followed by stirring at room temperature for 48 h. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (600 ml) using a mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent affording 3.31 g (58%) of the title compound as an amorphous solid.

Workup

  1. temperatureat reflux temperature for 10 h
  2. stirringby stirring at room temperature for 48 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (600 ml)
  5. additiona mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent

Sources & evidence

ORD record
ord-69f3dabb095b47be8fa6c8aa18d39b0b
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

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