Sodium hydride → 6-Chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-7-[2-(1-pyrrolidinyl)ethoxy]-1H-imidazo[4,5-b]pyridine

HRID 2218399Notes

Reaction equation

HRID 2218399 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[OH:27][CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.[H-].[Na+]>CC#N>[Cl:1][C:2]1[C:3]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 178478272HCID 178478272, compound

Product 1

HCID 100277626-Chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-7-[2-(1-pyrrolidinyl)ethoxy]-1H-imidazo[4,5-b]pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (0.010 g, 0.025 mmol), 1-(2-hydroxyethyl)pyrrolidine (0.5 ml) and sodium hydride were heated to 120° C. for 3 h. The reaction mixture was diluted with CH3CN and purified by HPLC-C18, giving the title product (0.006 g, 50%)

Workup

  1. custompurified by HPLC-C18

Sources & evidence

ORD record
ord-94032e7cafa442aea92f692c6960fa70
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

Loading…