Ammonium Chloride → HCID 24763458, compound

Participants

Reaction Conditions

Reaction Steps

In a dried vessel, 82 mg (0.55 mMol) 3-tert-butyl-aniline are dissolved in 8 ml toluene and cooled in an ice bath. Then 825 μl Me3Al (2 M in toluene; 1.65 mMol) are added via syringe. After 1¼ h at rt, a solution of 107 mg (0.25 mMol) 6-(2-hexanoyloxymethyl-pyrimidin-4-yloxy)-benzo[b]thiophene-3-carboxylic acid ethyl ester (Step 17.5) in 1 ml THF is added and the solution is stirred for 1 h in an oil bath of 110° C. The solution is cooled in an icebath and hydrolyzed with 16 ml of a sat. NH4Cl solution. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 9:1→1:1→EtOAc) gives the title compound: Anal. (+0.3H2O): C,H,N,S; MS: [M+1]+=434; TLC(hexane/EtOAc 1:2): Rf=0.31; 1H MNR (DMSO-d6): δ ppm 10.32 (s, HN), 8.67 (d, 1H), 8.58 (s, 1H), 8.46 (d, 1H), 8.03 (s, 1H), 7.76 (s, 1H), 7.68 (d, 1H), 7.35 (d, 1H), 7.28 (t, 1H), 7.15 (d, 1H), 6.98 (d, 1H), 5.18 (sb, HO), 4.41 (s, CH2), 1.31 (s, 9H).

Provenance & Evidence