AR-R-17779 → (R)-3'-[5-(4-Pyridyl)-1,3,4-thiadiazol-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109473

Reaction equation

HRID 2109473 reaction equation
[O:1]1[C@@:5]2([CH:10]3[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]3)[CH2:6]2)[CH2:4][NH:3][C:2]1=[O:13].Br[C:15]1[S:16][C:17]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1>[Cu]I>[N:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:16][C:15]([N:3]3[CH2:4][C@:5]4([CH:10]5[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]5)[CH2:6]4)[O:1][C:2]3=[O:13])=[N:19][N:18]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5310971AR-R-17779HCID 576342624-(5-Bromo-1,3,4-thiadiazol-2-yl)pyridine

Product 1

HCID 57634239(R)-3'-[5-(4-Pyridyl)-1,3,4-thiadiazol-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

The compound was prepared by a method analogous to that described in Preparation 3 from (S)-spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and 2-bromo-5-(4-pyridyl)-1,3,4-thiadiazole using 5 equivalents of copper (I) iodide. The title compound was obtained as a beige solid, m/z 344 (MH+).

Workup

  1. customThe compound was prepared by a method analogous to

Sources & evidence

ORD record
ord-6cd73dd400094eafb4407b0753ba021b
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Linked notes

Loading…