1-Propanol → HCID 178504130, compound

HRID 537893Notes

Reaction equation

HRID 537893 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)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1.[CH2:30](O)CC>>[CH3:30][SH:10]([CH2:17][C:18]1[NH:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1)[C:9]1[N:11]=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][N:3]2[N:8]=1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 15334493Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amideHCID 591512282-Chloromethyl-1-methyl-4-phenyl-1H-imidazole

Product 1

HCID 178504130HCID 178504130, compoundYield 62%

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-1-methyl-4-phenyl-1H-imidazole 6 (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=322.1 (MH+), tR=2.29 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-8c94d8ab565347a49093eb8ce356c31f
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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