Sodium Iodide → HCID 68668001, compound

HRID 342159Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[NH:9][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:11][N:12]=1)(=O)=O.[Cl:22][C:23]1[CH:28]=C[CH:26]=[CH:25][C:24]=1C1NCCNC1=O.[I-].[Na+].C[CH2:39][N:40](C(C)C)[CH:41](C)C.[CH3:47][N:48]([CH:50]=[O:51])[CH3:49]>>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:10]2[NH:9][C:8]([CH:7]([N:40]3[CH2:41][CH2:47][N:48]([C:49]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:22])[CH:28]=4)[C:50](=[O:51])[CH2:39]3)[CH3:6])=[N:12][CH:11]=2)=[CH:15][CH:16]=1)#[N:21]

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 542578272-Piperazinone, 3-(2-chlorophenyl)-

HCID 54501257HCID 54501257, compound

Product 1

HCID 68668001HCID 68668001, compound

Conditions

Temperature: 55 °C

Procedure

A solution of 2-(-5-(4-cyanobenzyl)-imidazolyl)ethyl methanesulfonate (24 mg, 0.079 mmol) in DMF (0.2 ml) was added to 3-(chlorophenyl)piperazin-2-one (17.7 mg, 0.084 mmol), sodium iodide (50 mg, 0.336 mmol) and Hunigs base (0,0146 ml, 0.084 mmol). The mixture was stirred at 55° C. for 12 hours, and the solvent evaporated in vacuo. The residue was purified by preparative tic eluting with 10% saturated ammonia/acetonitrile to afford the title compound. 1H NMR δ CDCl3 (7.61 (2H, d, J=8.4 Hz), 7.56 (1H, s), 7.35-7.20 (7H, m), 7.16 (1H, d, J=8 Hz), 6.85 (1H, s), 4.03 (2H, s), 3.83 (2H, t, J=6.5 Hz),3.61 (2H, t, J=5.4 Hz), 3.27 (2H, s), 2.68 (2H, t, J=5.4 and 2.57 (2H, t, J=6.5 Hz) ppm.

Workup

customthe solvent evaporated in vacuo
customThe residue was purified by preparative
washtic eluting with 10% saturated ammonia/acetonitrile

Sources & evidence

ORD record: ord-167674decc114e04b0696c6fccbfeb68
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856326

Reaction notes

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