Triethylamine → 2-(4-Chloro-2-cyanato-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

HRID 11723

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH3:24])=[O:9])=[C:4]([OH:27])[CH:3]=1.[CH2:28]([N:30](CC)CC)C.N#CBr>C(Cl)Cl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH3:24])=[O:9])=[C:4]([O:27][C:28]#[N:30])[CH:3]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.168 g, 0.427 mmol) in methylene chloride (2 mL) was added triethylamine (0.12 mL, 0.86 mmol). The solution was cooled to −5° C. via an acetone/ice bath then cyanogen bromide was added (0.22 mL, 0.66 mmol). The reaction was stirred at −5° C. for 30 minutes then concentrated in vacuo to give the crude title compound which was taken directly on to the next step (0.17 g).

Workup

concentrationthen concentrated in vacuo

Sources & evidence

ORD record: ord-43200a14bd5d42a5942f72c148bce99b
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Linked notes

Loading…