2-Pentanone → HCID 178446244, compound
Reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:11][C:12](=O)[CH2:13][CH2:14][CH3:15].[BH4-].[Na+]>>[CH3:11][CH:12]([NH:10][C:8]1[CH:7]=[CH:6][C:5]2[NH:1][CH:2]=[N:3][C:4]=2[CH:9]=1)[CH2:13][CH2:14][CH3:15]Participants
4
Procedure
The compound was synthesized starting from benzimidazol-5-amine (399 mg; 3 mmol; 1 eq.), 2-pentanal (284 mg; 0.351 ml; 3.3 mmol; 1.1 eq) and NaBH4 (228 mg; 6 mmol; 2 eq.) as described in method 3; Yield: 0.264 g (43.3%); MS m/z: 204.4 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 0.88 (t, 3H, 3J=7.5 Hz); 1.10 (d, 3H, 3J=6.2 Hz); 1.32-1.42 (m, 3H); 1.49-1.56 (m, 1H); 3.35-3.37 (m, 1H); 5.02 (br s, 1H); 6.52-6.55 (m, 2H); 7.25 (d, 1H, 3J=8.7 Hz); 7.83 (s, 1H); 11.81 (br s, 1H); HPLC (METHOD [A]): rt 7.79 min (80.5%)
Workup
- custom