Ammonium Chloride → HCID 10087836, compound

Participants

Reaction Steps

To a suspension of 344 mg CeCl3 in 3 mL dry THF at −78° was added 0.70 mL 2 M benzylmagnesium chloride and the reaction was stirred 1.5 h under Ar. Then, 41 mg of 3-amino-4-formyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (see Example 16) was added and the reaction was stirred 3.5 h in the cold and then allowed to warm to room temperature over 0.5 h. Aqueous NH4Cl was added and the reaction was filtered through diatomaceous earth, washing with EtOAc, and the aqueous phase was separated and extracted 3 times more with EtOAc. The combined organics were dried, concentrated in vacuo, and re-dissolved in EtOAc with a trace MeOH and washed 3 times with aqueous NaHSO3. This was dried, concentrated in vacuo, and the product was purified on a prep plate developed with 5% MeOH—CH2Cl2. The product was re-dissolved in MeOH—CH2Cl2, filtered, concentrated and dried in vacuo at 60° C. providing 16.3 mg of the title compound as an orange solid.

Provenance & Evidence