Chloroform → (+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(3-methoxy-azetidin-1-yl)-isonicotinamide

HRID 985821Notes

Reaction equation

HRID 985821 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([CH:17]3[CH2:22][O:21][CH2:20][CH2:19][O:18]3)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[CH3:35][O:36][CH:37]1[CH2:40][NH:39][CH2:38]1.C(Cl)(Cl)Cl>CN(C=O)C>[O:18]1[CH2:19][CH2:20][O:21][CH2:22][CH:17]1[C:16]1[C:10]2[S:9][C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:25]=[CH:26][N:27]=[C:2]([N:39]4[CH2:40][CH:37]([O:36][CH3:35])[CH2:38]4)[CH:3]=3)=[N:12][C:11]=2[C:13]([O:23][CH3:24])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10796Cesium carbonateHCID 222428583-Methoxyazetidine hydrochlorideHCID 22507693(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 11487896(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(3-methoxy-azetidin-1-yl)-isonicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide with cesium carbonate and 3-methoxy-azetidine hydrochloride in DMF. [α]D20=+42.5° (c=0.44, CHCl3), ES-MS m/e (%): 457 (M+H+, 100).

Sources & evidence

ORD record
ord-33dabb80d3a34c53a3e4bbe69a97eebe
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

Loading…