Ethanolamine → HCID 69883411, compound

Participants

Reaction Conditions

Reaction Steps

Ethanolamine (47 mg, 2.5 eq) was added to a solution of (R)-N-(2-chloro-3-fluoro-4-{4-fluorophenylsulphonyl}phenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 11) (135 mg) in NMP (1 ml) and the mixture was stirred and heated (oil bath 120° C.) under argon for 24 hours. The reaction mixture was cooled and partitioned between a saturated aqueous solution of ammonium chloride (10 ml) and ether (3×20 ml). The combined ether extracts were washed with water (50 ml), dried and concentrated to give a gum. The residue was dissolved in MeOH/DCM and loaded onto deactivated silica (1 g). It was then concentrated to give a free flowing powder which was poured onto an ISOLUTE column (10 g silica) and chromatographed eluting with EtOAc/isohexane to give the title compound (50 mg) as a gum. NMR: 1.65 (s, 3H), 3.2 (m, 2H), 3.42 (m, 2H), 4.92 (t, 1H), 5.91 (t, 1H), 7.47 (t, 2H), 7.89 (d, 1H), 7.96-8.08 (m, 3H), 9.85 (brs, 1H); m/z: 483.

Provenance & Evidence