Trifluoroacetic acid → HCID 66604633, compound

Participants

Reaction Steps

Diethyl azodicarboxylate (0.076 mL, 0.48 mmol) was added to a solution of triphenylphosphine (126 mg, 0.482 mmol), 2-(3-chloro-4-hydroxyphenyl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (70 mg, 0.16 mmol) and 2-morpholinoethanol (0.039 mL, 0.32 mmol) in dry THF (2 mL) in an oven-dried vial at RT under nitrogen. After stirring for 12 h, preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min). SCX capture and release with 2 N NH3 in MeOH afforded 2-(3-chloro-4-(2-morpholinoethoxy)phenyl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (25 mg, 0.041 mmol, 26% yield) as a yellow solid. 1H NMR and LCMS are consistent with the desired material. MS (ESI) m/z 549.23 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.83 (1H, s), 8.27 (1H, d, J=8.55 Hz), 8.16 (1H, d, J=1.53 Hz), 8.00 (1H, dd, J=8.24, 1.83 Hz), 7.60 (1H, s), 7.08 (1H, d, J=8.24 Hz), 7.02 (1H, dd, J=8.70, 1.98 Hz), 6.93-6.96 (1H, m), 4.26-4.30 (2H, m), 3.76-3.81 (4H, m), 3.40-3.45 (4H, m), 2.90-2.95 (2H, m), 2.65-2.73 (8H, m), 2.44 (3H, s).

Provenance & Evidence