1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-2-Amino-N-{4-[(4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-propionamide

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Reaction Steps

[(S)-1-({4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-carbamoyl)-ethyl]-carbamic acid tert-butyl ester: To (2-aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (210 mg, 0.74 mmol), Boc-L-Ala-OH (140 mg, 0.74 mmol), EDCI (170 mg, 0.89 mmol) and HOBt-hydrate (136 mg, 0.89 mmol) in DMF (3 mL) was added ethyl-diisopropyl-amine (383 μL, 2.2 mmol). The reaction was stirred at room temperature overnight, diluted with EtOAc and quenched with 10% aqueous HCl followed by saturated aqueous NaHCO3. The aqueous phase was extracted with EtOAc (4×15 mL). The combined organic phases were washed with brine, dried (MgSO4) and concentrated. Purification by gradient MPLC (0-20% MeOH/CH2Cl2 with 0.1% NH4OH) gave 285 mg (83%) of the title compound as a yellow solid. 1H NMR (MeOH-d4) δ 7.69 (d, 1H), 7.61-7.57 (m, 1H), 7.1 (d, 2H), 7.03-6.98 (m, 4H), 4.61-4.49 (m, 2H), 4.23 (q, 1H), 3.83 (s, 3H), 3.62 (s, 3H), 1.44 (s, 9H), 1.4 (d, 3H); LC-MS (ESI+; 466 ([M+H]+)).

Provenance & Evidence