1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl[2-[n-[1-(1h-pyrrolo[2,3-c]pyridin-2-yl)ethyl]carbamoyl]ethyl]carbamate

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Reaction Steps

A mixture of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylamine dihydrochloride (Example 75) (108 mg, 0.46 mmol), N-Boc-β-alanine (71 mg, 0.37 mmol), diisopropylethylamine (0.31 mL, 1.85 mmol), EDCI (78 mg, 0.41 mmol) and HOBt (catalytic amount) in methylene chloride (2.2 mL) was stirred at room temperature under a nitrogen atmosphere overnight (22 h). The reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in CH2Cl2, washed with water and saturated NaHCO3, and dried over Na2SO4. Filtration and concentration provided tert-butyl[2-[N-[1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethyl]carbamoyl]ethyl]carbamate (70 mg, 58%) as a tan solid: 1H NMR (500 MHz, CD3OD) δ1.45 (9H, s), 1.63 (3H, d), 2.37-2.51 (2H, m), 3.30-3.42 (2H, m), 5.26-5.35 (1H, m), 6.43 (1H, s), 7.48-7.51 (1H, m), 7.99-8.05 (1H, m), 8.60 (1H, s); ESI MS m/z 333 [C17H24N4O3+H]+; HPLC (Method A) 95.9% (AUC), tR=14.39 min.

Provenance & Evidence