Chloroform → (+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(2-methoxy-ethoxy)-isonicotinamide

HRID 985850Notes

Reaction equation

HRID 985850 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][N:29]=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[C:18]([CH:19]3[CH2:24][O:23][CH2:22][CH2:21][O:20]3)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=2[N:14]=1)=[O:8].[CH3:30][O:31][CH2:32][CH2:33][OH:34].C(Cl)(Cl)Cl>O1CCOCC1.CN(C=O)C>[O:20]1[CH2:21][CH2:22][O:23][CH2:24][CH:19]1[C:18]1[C:12]2[S:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:27]=[CH:28][N:29]=[C:4]([O:34][CH2:33][CH2:32][O:31][CH3:30])[CH:5]=3)=[N:14][C:13]=2[C:15]([O:25][CH3:26])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 80192-MethoxyethanolHCID 23670120(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide sodium hydride

Product 1

HCID 22507763(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(2-methoxy-ethoxy)-isonicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

From (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide sodium hydride and 2-methoxyethanol in dioxane and DMF. [α]D20=+17.6° (c=0.15, CHCl3), ES-MS m/e (%): 446 (M+H+, 100).

Sources & evidence

ORD record
ord-887d25a5daa845888f81021e3ec18c62
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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