Dimethyl Sulfoxide → HCID 11305295, compound

HRID 985838Notes

Reaction equation

HRID 985838 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.[NH:35]1[CH2:38][CH:37]([OH:39])[CH2:36]1.CS(C)=O>CN1C(=O)CCC1>[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:35]4[CH2:38][CH:37]([OH:39])[CH2:36]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 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 22507693(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 11305295HCID 11305295, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

From (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide with cesium carbonate and azetidin-3-ol hydrochloride in NMP. [α]D20=+12.2° (c=0.51, DMSO), ES-MS m/e (%): 443 (M+H+, 100).

Sources & evidence

ORD record
ord-c947abef376147a39420057ab067e863
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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