Acetonitrile → HCID 22624307, compound

HRID 279068Notes

Reaction equation

HRID 279068 reaction equation
[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[I-].[CH3:27][S+](C)C.[OH-].[K+].C(#N)C>O>[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:27][O:21]3)=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])[N:9]=1)=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 75127Trimethylsulfonium iodideHCID 22624290HCID 22624290, compound

Product 1

HCID 22624307HCID 22624307, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 2.99 g (8.79 mmol) N-t-butylcarbonyl-6-(2-isopropoxy-4-formylphenyl)-pyridin-2-ylamine, 1.79 g (8.79 mmol) trimethylsulfonium iodide, 0.98 9 (17.59 mmol) powdered potassium hydroxide, 44 mL acetonitrile, and 0.5 mL water. The reaction was heated to 60° C. for 2.5 hours, then cooled, filtered, and evaporated. The yellow oil was used directly, 3.3 g (˜100%).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-11253d961f184609b01398af28edd9ce
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Reaction notes

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