Potassium Iodide → 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric acid ethyl ester

HRID 11718

Reaction equation

[NH2:1][C:2]1[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][C@H:17]([CH3:19])[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:15][C@H:14]2[CH3:28])=[O:12])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35]Br)[CH3:30].C(=O)(O)[O-].[Na+].[I-].[K+].C(OC(=O)C(Br)CC)C>C(O)C>[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35][NH:1][C:2]1[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][C@H:17]([CH3:19])[N:16]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH2:15][C@H:14]2[CH3:28])=[O:12])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH3:30]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(3-amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.072 g, 0.18 mmol) in ethanol (1 mL) was added 4-bromo-butyric acid ethyl ester (0.030 mL, 0.21 mmol), sodium bicarbonate (0.031 g, 0.37 mmol) and potassium iodide (˜0.030 g). The resulting solution was stirred at 70° C. for 18 hours. Additional bromo-butyric acid ethyl ester (0.030 mL, 0.21 mmol) was added and the reaction was stirred at 70° C. for 18 hours. The reaction was cooled, concentrated in vacuo and purified via flash chromatography on silica gel to give the title compound (0.034 g).

Workup

stirringthe reaction was stirred at 70° C. for 18 hours
temperatureThe reaction was cooled
concentrationconcentrated in vacuo
custompurified via flash chromatography on silica gel

Sources & evidence

ORD record: ord-5c62ce052f7a4c5586df582a6416f915
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Linked notes

Loading…