Ethanol → HCID 11965020, compound

HRID 1890502Notes

Reaction equation

HRID 1890502 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]([C:16]2[C:17]([S:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26](S(C)=O)[N:25]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[CH:9]=[C:10]([CH3:12])[CH:11]=1.C(O)C>C(OCC)(=O)C>[CH:1]1([NH:4][C:26]2[N:25]=[C:24]([CH2:23][S:22][C:17]3[C:16]([C:14]([NH:13][C:8]4[CH:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH3:5])[CH:7]=4)=[O:15])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:29]=[CH:28][N:27]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 69828CyclopropylamineHCID 67161373HCID 67161373, compound

Product 1

HCID 11965020HCID 11965020, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropylamine (6.0 mL) was added to N-(3,5-dimethylphenyl)-2-(2-methylsulfinylpyrimidin-4-ylmethylthio) pyridine-3-carboxamide (990 mg, 2.4 mmol, Compound No. 1-27), and the mixture was stirred for 30 minutes at 80° C. The reaction mixture was diluted with ethyl acetate (80 mL), washed twice with water (50 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, then the residue was purified by silica gel column chromatography to give 650 mg (recrystallized from ethanol) of the target compound as a colorless solid (Yield: 67%).

Workup

  1. washwashed twice with water (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customto give

Sources & evidence

ORD record
ord-9ac51055502c4cd0aff8cd9afd012f67
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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