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 2175361Notes

Reaction equation

HRID 2175361 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 96/01826 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-aad687e2b4a8416d97bf9378daa057ea
Source dataset
uspto-grants-2015_06
Patent number
US09062060B2

Reaction notes

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