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

HRID 985847Notes

Reaction equation

HRID 985847 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].[F:30][C:31]([F:35])([F:34])[CH2:32][OH:33].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:33][CH2:32][C:31]([F:35])([F:34])[F: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 64092,2,2-TrifluoroethanolHCID 23670120(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide sodium hydride

Product 1

HCID 22507705(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(2,2,2-trifluoro-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 2,2,2-trifluoroethanol in dioxane and DMF. [α]D20=+11.3° (c=0.11, CHCl3), ES-MS m/e (%): 470 (M+H+, 100).

Sources & evidence

ORD record
ord-9c189717ef1d4bebbb270ad03b1e8d1b
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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