Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amide → 2-([1,2,4]triazolo[1,5-a]pyridin-2-ylsulfanylmethyl)-5H-imidazo[2,1-a]isoindole

HRID 2401523Notes

Reaction equation

HRID 2401523 reaction equation
N=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[NH:8][C:9]([N:11]1C=CN=C1)=[S:10].Cl[CH2:17][C:18]1[N:19]=[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][N:21]2[CH:29]=1>C(O)CC>[N:11]1[C:9]([S:10][CH2:17][C:18]2[N:19]=[C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][N:21]3[CH:29]=2)=[N:8][N:3]2[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=12

Participants

4

Reactant 2

HCID 15334493Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amideHCID 696709702-Chloromethyl-5H-imidazo[2,1-a]isoindole

Product 1

HCID 696707612-([1,2,4]triazolo[1,5-a]pyridin-2-ylsulfanylmethyl)-5H-imidazo[2,1-a]isoindoleYield 62.4%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

An adaptation of the method described in WO 96801826 was used, Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amide (200 mg, 1.37 mmol) and 2-Chloromethyl-5H-imidazo[2,1-a]isoindole (300 mg, 1.46 mmol) were dissolved in 1-propanol (25 mL) and the mixture was heated to reflux for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with water and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel to afford the title compound (273 mg, 62%) as a yellow solid. LC-MS: m/z=321.1 (MH+), tR=1.40 min, method B.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. washThe solution was washed with water
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5419bace10e445e6ae2c8c327d6bd6ee
Source dataset
uspto-grants-2014_08
Patent number
US08796304B2

Reaction notes

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