Sodium Azide → HCID 178418849, compound

HRID 11727Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[Cl-].[Cl-].[Al+3].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][C:23]([N:25]2[CH2:30][C@H:29]([CH3:31])[N:28]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH2:27][C@H:26]2[CH3:40])=[O:24])=[C:14]([C:16](=[O:20])[CH2:17][C:18]#[N:19])[CH:15]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CS(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][C:23]([N:25]2[CH2:30][C@H:29]([CH3:31])[N:28]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)[CH2:27][C@H:26]2[CH3:40])=[O:24])=[C:14]([C:16](=[O:20])[CH2:17][C:18]2[NH:19][N:3]=[N:2][N:1]=2)[CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of sodium azide (0.061 g, 0.95 mmol) and aluminum trichloride (0.042 g, 0.31 mmol) was added 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-3-oxo-propionitrile (0.035 g, 0.076 mmol) in tetrahydrofuran (2 mL). The reaction was warmed to 70° C. and stirred for 18 hours. To this was added saturated aqueous sodium bicarbonate (0.5 mL) and dimethylsulfoxide (0.5 mL) and the solution was stirred for 1 hour at ambient temperature. The solids were removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified by reverse phase HPLC to give the title compound which was converted to its hydrochloride salt (0.020 g, LRMS: 501.2).

Workup

stirringthe solution was stirred for 1 hour at ambient temperature
customThe solids were removed by filtration
concentrationthe filtrate was concentrated in vacuo
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-4771e08e0b5c4ac886d5b76ef3b2fdcb
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Reaction notes

Loading…