Triethylamine → HCID 178522149, compound

Participants

Reaction Steps

345 mg (1.23 mMol) 6-(6-hydroxy-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (Step 3.8), 193 μl (1.5 mMol) 4-fluoro-3-trifluoromethyl-aniline, 1.7 ml (12.3 mMol) Et3N and 63 mg (0.52 mMol) DMAP are dissolved in 10 ml of dry DMF. Then a solution of 1.45 ml (50% in DMF; 2.48 mMol) propylphosphonic anhydride is added. After 20 min, the reaction mixture is poured into water, brine and EtOAc. The separated aq. phase is extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2→CH2Cl2/MeOH 1:19) gives the title compound: MS: [M+1]+=442; TLC (CH2Cl2/MeOH 1:9): Rf=0.37; 1H-NMR (DMSO-d6): δ ppm 12.43 (s, 1H), 10.92 (s, HN), 8.36 (m, 1H), 8.17 (d, 1H), 8.11 (m, 3H), 7.92 (s, 1H), 7.78 (d, 1H), 7.7-7.5 (m, 3H), 6.25 (s, 1H), 3.99 (s, H2C).

Provenance & Evidence