Formaldehyde → HCID 69284565, compound

Participants

Reaction Steps

The sample of the trifluoroacetic acid salt of N-(2-((1S,2R,4R)-4-amino-2-((pyridin-3-yloxy)methyl)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide prepared in Example 5c, Step 2 was dissolved in methanol (3 mL) and treated sequentially with acetone (ca. 1 mL) and sodium cyanoborohydride (28 mg). The mixture was stirred at rt for 3 h. Aqueous formaldehyde (ca. 1 mL) was added and the mixture was stirred at rt for 3 days. The mixture was concentrated under vacuum and the residue was taken up in ethyl acetate and saturated aqueous NaHCO3. The phases were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated. Purification by reverse phase HPLC and lyophilization provided the bis-trifluoroacetic acid salt of the title product, N-(2-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-((pyridin-3-yloxy)methyl)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide, as a white powder (10 mg). MS found: (M+H)+=507.2.

Provenance & Evidence