Hydrochloric Acid → HCID 58408410, compound

HRID 1948566Notes

Reaction equation

HRID 1948566 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)=[C:12]([CH:18]=2)[C:13]([O:15]CC)=[O:14])[CH:5]=[N:6][CH:7]=1.[OH-].[Li+].Cl>C(O)(C)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)=[C:12]([CH:18]=2)[C:13]([OH:15])=[O:14])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58408408HCID 58408408, compound

Product 1

HCID 58408410HCID 58408410, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl 5-(5-methylpyridin-3-yl)-2-pyrazin-2-ylbenzoate (3-3, 0.065 g, 0.204 mmol, 1.0 equiv) in isopropanol/water (3:1, 2 mL) was added 1M lithium hydroxide solution (0.244 mL, 0.244 mmol, 1.2 equiv) and the reaction was heated to 60° C. for 30 minutes in the microwave. The reaction mixture was cooled and the pH was adjusted to ˜7 by the addition of 1N HCl. The reaction mixture was concentrated and the solids azeotroped from toluene to afford the product (3-4) as a solid. ESI+ MS [M+H]+ C17H13N3O2: 292.1 found, 292.31 required.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationThe reaction mixture was concentrated
  3. customthe solids azeotroped from toluene

Sources & evidence

ORD record
ord-d922bd8df00c408daa9c4a5742524f02
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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