Cesium carbonate → 5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-furan-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole

HRID 732084Notes

Reaction equation

HRID 732084 reaction equation
COC1C=C(C2ON=C(CSC3NC4C=CC=CC=4N=3)N=2)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:31][C:32]1[S:36][CH:35]=[C:34]([C:37]2[O:41][N:40]=[C:39]([CH2:42]ON3C4C=CC=CC=4N=N3)[N:38]=2)[CH:33]=1.[CH2:53]([N:55]1[C:59]([C:60]2[O:61][CH:62]=[CH:63][CH:64]=2)=[N:58][NH:57][C:56]1=[S:65])[CH3:54]>CCCCCCC.CCOC(C)=O>[Cl:31][C:32]1[S:36][CH:35]=[C:34]([C:37]2[O:41][N:40]=[C:39]([CH2:42][S:65][C:56]3[N:55]([CH2:53][CH3:54])[C:59]([C:60]4[O:61][CH:62]=[CH:63][CH:64]=4)=[N:58][N:57]=3)[N:38]=2)[CH:33]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6610424-Ethyl-5-furan-2-yl-4H-(1,2,4)triazole-3-thiolHCID 98408012-[5-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-1H-benzoimidazoleHCID 670705901-[5-(5-chloro-thiophen-3-yl)-[1,2,4]oxadiazol-3-ylmethoxy]-1H-benzotriazole

Product 1

HCID 670706085-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-furan-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

The title compound was prepared according to method for 2-[5-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-1H-benzoimidazole, with the exception of using molar equivalent cesium carbonate instead of potassium carbonate as the base, from 1-[5-(5-chloro-thiophen-3-yl)-[1,2,4]oxadiazol-3-ylmethoxy]-1H-benzotriazole (32.3 mg, 0.097 mmol) and 4-ethyl-5-furan-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione (23 mg) by using 50% EtOAc in n-heptane as chromatography eluent to yield 21 mg. 1H NMR (CDCl3) d (ppm): 7.95 (d, 1H), 7.57 (dd, 1H), 7.44 (d, 1H), 7.07 (dd, 1H), 6.56 (dd, 1H), 4.56 (s, 2H), 4.22 (q, 2H), 1.35 (t, 3H).

Workup

  1. customto yield 21 mg

Sources & evidence

ORD record
ord-8f2bdbb666144882b5fdf4646840ace4
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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