Formaldehyde → HCID 86691894, compound

To a solution of (3R)-3-methylmorpholine (51.6 mg, 0.510 mmol, Tyger Scientific, Ewing, USA) in methanol (2 mL) was added formaldehyde (37% aqueous) (0.038 mL, 0.510 mmol). The reaction mixture was stirred at room temperature for 1 hour before the addition of 4-isocyano-2-(trifluoromethyl)benzonitrile (100 mg, 0.510 mmol, commercially available from Priaxon AG, Munich, Germany) and trimethylsilylazide (0.068 mL, 0.510 mmol). The reaction mixture was stirred at room temperature overnight (approximately 18 hours) and the solvent removed under vacuum. The residue was purified by MDAP. Fractions containing the desired compound were combined and the solvent removed. The residue was partitioned between saturated NaHCO3 (2 mL) and DCM (5 ml). The organic layer was collected via a hydrophobic frit and the solvent removed under a stream of argon. The compound was dissolved in a minimum of diethyl ether before the addition of 1N HCl in diethyl ether (2 mL) leading to precipitation. The ether was removed under vacuum and the product further dried under vacuum at 40° C. overnight to yield the title compound as a white solid (57 mg).

1. customthe solvent removed under vacuum
2. customThe residue was purified by MDAP
3. additionFractions containing the desired compound
4. customthe solvent removed
5. customThe residue was partitioned between saturated NaHCO3 (2 mL) and DCM (5 ml)
6. customThe organic layer was collected via a hydrophobic frit
7. customthe solvent removed under a stream of argon
8. dissolutionThe compound was dissolved in a minimum of diethyl ether before the addition of 1N HCl in diethyl ether (2 mL)
9. customleading to precipitation
10. customThe ether was removed under vacuum
11. customthe product further dried under vacuum at 40° C. overnight

ORD record

ord-7553ba9e09ab4a698a9f520f206438f6

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115132B2