Triethylamine → 5-{2-[4-(5,6,7,8-Tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazin-1-yl]ethyl}-2-benzofuran-1(3H)-one

HRID 1519601Notes

Reaction equation

HRID 1519601 reaction equation
Cl.[N:2]1([CH:8]2[CH2:20][CH2:19][C:18]3[C:10](=[CH:11][C:12]4[C:13]([CH:17]=3)=[N:14][O:15][N:16]=4)[CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:27]2[C:28](=[O:31])[O:29][CH2:30][C:26]=2[CH:25]=1.C(N(CC)CC)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N:14]1[O:15][N:16]=[C:12]2[CH:11]=[C:10]3[C:18]([CH2:19][CH2:20][CH:8]([N:2]4[CH2:3][CH2:4][N:5]([CH2:22][CH2:23][C:24]5[CH:33]=[CH:32][C:27]6[C:28](=[O:31])[O:29][CH2:30][C:26]=6[CH:25]=5)[CH2:6][CH2:7]4)[CH2:9]3)=[CH:17][C:13]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 675131635-(2-Bromoethyl)-2-benzofuran-1(3H)-oneHCID 866944496-Piperazin-1-yl-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazole hydrochloride

Product 1

HCID 680716775-{2-[4-(5,6,7,8-Tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazin-1-yl]ethyl}-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 6-Piperazin-1-yl-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazole hydrochloride (20 mg, 0.068 mmol), 5-(2-bromoethyl)-2-benzofuran-1(3H)-one (33 mg, 0.14 mmol), and tetrabutylammonium iodide (2.5 mg, 6.8 umol) in DMF (2 mL) was added triethylamine (0.028 mL, 0.20 mmol). The mixture was heated to 55° C. for 6 hours. LC showed formation of the desired product, which was separated by mass-directed HPLC. LC-MS (IE, m/z): 419 [M+1]+. (0.21 μM)

Sources & evidence

ORD record
ord-89d291171bcb478194f7939caa2ef695
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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