Benzylethanolamine → 2-[Benzyl(6-chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl)-1H-imidazo[4,5-b]pyridin-7-yl)amino]ethanol

HRID 2218394Notes

Reaction equation

HRID 2218394 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.[CH2:27]([NH:34][CH2:35][CH2:36][OH:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC#N>[CH2:27]([N:34]([C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:15][CH:16]=3)[NH:10][C:4]=12)[CH2:35][CH2:36][OH:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 4348BenzylethanolamineHCID 178478272HCID 178478272, compound

Product 1

HCID 104139182-[Benzyl(6-chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl)-1H-imidazo[4,5-b]pyridin-7-yl)amino]ethanol

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) (0.10 g, 0.25 mmol) and N-benzylethanolamine (0.3 g) were heated to 180° C. for 15 h. The reaction mixture was diluted with CH3CN and purified by HPLC-C18 to deliver the title product as the bis(trifluoroacetate) (44%).

Workup

  1. custompurified by HPLC-C18

Sources & evidence

ORD record
ord-bc41518ee02c4978bcf3aabc81a0a178
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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