Aluminium lithium hydride → HCID 59394155, compound

Participants

Reaction Steps

LiAlH4 (0.46 mL, 1.0 M THF) is added to a solution of {6-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl}-acetic acid methyl ester (0.125 g, 0.232 mmol) in THF (5 mL). After 0.5 h the excess LiAlH4 is quenched by the addition of saturated aqueous NH4Cl. Workup is done with saturated aqueous NH4Cl and DCM (25 mL each). The residue is then separated via semi-prep HPLC to give 5-[7-(2-hydroxy-ethyl)-6-methyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yloxy]-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide. MS (ESI) m/z 512.3 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (s, 1 H), 8.30 (d, J=8.6 Hz, 1 H), 8.11 (d, J=3.5 Hz, 1 H), 8.09 (s, 1 H), 7.94 (d, J=8.3 Hz, 1 H), 7.57-7.65 (m, 1 H), 7.41-7.46 (m, 2 H), 7.11 (dd, J=9.0, 2.4 Hz, 1 H), 6.72-6.78 (m, 1 H), 4.47 (t, J=5.4 Hz, 1 H), 3.75 (s, 2 H), 3.57 (q, J=6.1 Hz, 2 H), 3.12-3.22 (m, 1 H), 2.88-3.00 (m, 1 H), 2.54-2.76 (m, 3 H), 1.10 (d, J=6.6 Hz, 3 H).

Provenance & Evidence