Dimethyl Sulfoxide → (+)-4-Hydroxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

HRID 985818Notes

Reaction equation

HRID 985818 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+].[OH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.CS(C)=O>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]([C:4]3[CH:25]=[CH:26][N:27]=[C:2]([N:38]4[CH2:39][CH2:40][CH:35]([OH:34])[CH2:36][CH2:37]4)[CH:3]=3)=[O:6])=[N:12][C:11]=2[C:13]([O:23][CH3:24])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 79341Piperidin-4-olHCID 22507693(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 86594654(+)-4-Hydroxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

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 4-hydroxypiperidine in DMF. [α]D20=+16.1° (c=0.35, DMSO), ES-MS m/e (%): 471 (M+H+, 100).

Sources & evidence

ORD record
ord-8f02a693f495417d8b44c26112156eee
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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