1,2-Dichloroethane → HCID 58760147, compound

Participants

Reaction Steps

The title compound was prepared from (3S)-1-(tert-butoxycarbonyl)-3-methyl-D-proline (15 mg, 0.07 mmol), N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 20 mg, 0.07 mmol, 1.0 equiv), EDC (19 mg, 0.10 mmol, 1.5 equiv) and HOAt (5 mg, 0.03 mmol, 0.5 equiv) in DMF (1 mL) followed by deprotection in TFA-CH2Cl2 essentially according to the procedure described in Example 27, Step C. Purification by reverse phase chromatography [95:5 water (+0.1% TFA)/CH3CN (+0.1% TFA) to 50:50 water (+0.1% TFA)/CH3CN (+0.1% TFA)] afforded the compound as a clear oil. 1H NMR (400 MHz, CDCl3): δ 9.10 (s, 1 H), 8.07–8.01 (m, 1 H), 7.56 (app s, 1 H), 7.41 (dd, J=1.6, 8.4 Hz, 1 H), 7.23 (d, J=8.4 Hz, 1 H), 4.65 (br s, 1 H), 4.57–4.55 (m, 1 H), 4.29 (dd, J=6.0, 15.6 Hz, 1 H), 4.05 (dd, J=5.2, 15.2 Hz, 1 H), 3.83–3.77 (m, 1 H), 3.62 (br s, 1 H), 3.45–3.38 (m, 2 H), 2.97 (br s, 1 H), 2.41–1.88 (m, 7 H), 1.01 (d, J=7.2 Hz, 3 H). HRMS (APCI) M+H: calcd for (C19H24N7O2Cl)+ 418.1753, found 418.1741.

Provenance & Evidence