Azetidine → (+)-2-Azetidin-1-yl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

HRID 985807Notes

Reaction equation

HRID 985807 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+].[NH:34]1[CH2:37][CH2:36][CH2:35]1>C(Cl)(Cl)Cl>[N:34]1([C:2]2[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=2)[C:5]([NH:7][C:8]2[S:9][C:10]3[C:16]([CH:17]4[CH2:22][O:21][CH2:20][CH2:19][O:18]4)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=3[N:12]=2)=[O:6])[CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 10796Cesium carbonateHCID 22507693(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 11487132(+)-2-Azetidin-1-yl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

From (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide with cesium carbonate and azetidine. [α]D20=+25.5° (c=0.26, CHCl3), ES-MS m/e (%): 427 (M+H+, 100).

Sources & evidence

ORD record
ord-53e66b7a415747fea1301a20b9abbf56
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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