Benzyl mercaptan → 7-(Benzylthio)-6-chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-1H-imidazo[4,5-b]pyridine

HRID 2218396Notes

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]([SH:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])(C)(C)C>CN(C=O)C.CCOC(C)=O>[CH2:27]([S: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[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:15][CH:16]=3)[NH:10][C:4]=12)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 80 °C

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), benzyl mercaptan (0.036 ml, 0.3 mmol) and potassum tert-butanolate (0.071 g, 0.63 mmol) were dissolved in DMF (1 ml) and heated to 80° C. for 48 h. The reaction mixture was diluted with EtOAc and extracted with 2M HCl. The aqueous phase was basified with 10M NaOH and extracted with EtOAc. The organic phase was dried (Na2SO4) and evaporated in vacuo and the residue was dissolved in CH3CN (3 ml) and purified by HPLC-C18, giving the title product as a bis(trifluoroacetate) (37%).

Workup

extractionextracted with 2M HCl
extractionextracted with EtOAc
dry with materialThe organic phase was dried (Na2SO4)
customevaporated in vacuo
dissolutionthe residue was dissolved in CH3CN (3 ml)
custompurified by HPLC-C18

Sources & evidence

ORD record: ord-5615784a05364f73ac9d25d072440454
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410966B2

Reaction notes

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