4-Morpholinecarbonyl chloride → 2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(morpholin-4-ylcarbonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine
Reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:15])[C:8]=2[N:16]=1)[CH3:2].[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:31]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:32])[CH2:23][CH2:24]2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:15])[C:8]=2[N:16]=1)[CH3:2]Participants
Procedure
Using the general method of Example 11 Part H, 2-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)-1H-imidazo[4,5-c]pyridin-4-amine (0.304 g, 0.917 mmol) was reacted with 4-morpholinecarbonyl chloride (0.107 mL, 0.917 mmol) to provide 0.250 g of 2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(morpholin-4-ylcarbonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine as an yellow orange solid, m.p. 158.1-160.5° C. Analysis: Calculated for C23H36N6O3: %C, 62.14; %H, 8.16; %N, 18.90; Found: %C, 62.02; %H, 7.94; %N, 18.99. 1H NMR (300 MHz, DMSO-d6) δ5.82 (s, 2 H), 4.64 (s, 2 H), 4.34-4.29 (m, 2 H), 3.62-3.54(m, 6 H), 3.50 (q, J=7.0 Hz, 2 H), 3.1 (t, J=4.4 Hz, 4 H), 2.74 (t, J=11.8 Hz, 2 H 2.38 (s, 3 H), 2.31 (s, 3 H), 1.67-1.55 (m, 5 H), 1.27-1.1 (m, 2H), 1.14 (t, J=7.0 Hz, 3 H); MS (CI) m/e 445.2935 (445.2927 calcd for C23H36N6O3, M+H).
Sources & evidence
- ORD record
- ord-16a92bd4bff041b08264c3865b9637a7
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06545017B1
Reaction notes
Loading…