Cyclopentylamine → HCID 58459108, compound

Participants

Reaction Steps

To a solution of crude (S)-2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxylic acid (132 mg, 0.36 mmol) in DMF (3 mL) was added cyclopentanamine (0.10 mL, 1.0 mmol), N-ethyl-N-isopropylpropan-2-amine (0.060 mL, 0.36 mmol) and 1 h-benzotriazol-1-yl-oxytripyrrolidinophosphonium (190 mg, 0.36 mmol). The resulting mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using 0 to 10% gradient of MeOH in DCM-EtOAc (1:1) with 0.2% NH4OH as eluent gave 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-N-cyclopentyl-1-cyclopropyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, MeOH-d4) δ 8.03 (1H, s), 7.70 (1H, d, J=8.0 Hz), 7.37 (1H, d, J=8.0 Hz), 7.28 (1H, t, J=8.0 Hz), 6.03 (1H, q, J=8.0 Hz), 4.45-4.38 (1H, m), 4.11 (1H, dd, J=8.0, 4.0 Hz), 3.53-3.44 (1H, m), 2.15-2.05 (2H, m), 1.88-1.78 (2H, m), 1.75-1.60 (4H, m), 1.38-1.10 (3H, m), 1.00-0.92 (1H, m); LC-MS (ESI) m/z 431.2 [M+H]+.

Provenance & Evidence